Merlic, Craig A.

Organic

Merlic Craig

Biography

Professor Merlic obtained his B.S. degree in Chemistry from the University of California, Davis in 1982. As a Fannie and John Hertz Foundation Graduate Fellow at the University of Wisconsin, Madison he earned his Ph.D. degree in Organic Chemistry in 1988. He was a National Institutes of Health Postdoctoral Fellow at Princeton University in the Department of Chemistry. He joined the faculty in the Department of Chemistry and Biochemistry at UCLA in 1989. He served as Vice Chair for the Department from 1997 to 2000 and 2004 to 2008. At UCLA, he has received a National Science Foundation Young Investigator Award, a Camille Dreyfus Teacher-Scholar Award, and an Alfred P. Sloan Research Fellowship in addition to several teaching awards.

Professor Merlic’s research focuses on applications of transition metal organometallic chemistry to organic synthesis and extends from catalysis to synthesis of new chemotherapeutic agents. He has invented new processes utilizing palladium and ruthenium catalysts, chromium arenes and carbenes, copper promoted coupling reactions, and devised an exceptionally efficient total synthesis of the calphostin family of protein kinase C inhibitors.

He created two award-winning Internet-based educational projects at UCLA. The first system, Virtual Office Hours, came online in 1995 and pioneered student-faculty communication through online question and answer sessions and delivery of instructional materials. The second project, WebSpectra, presents advanced nuclear magnetic resonance and infrared spectral problems in a unique manner and is used worldwide for teaching spectroscopy in organic chemistry.

Research Interests

Our research program encompasses synthetic organic, synthetic organometallic, and physical organometallic chemistry. Research goals include total synthesis of bioactive natural products, discovery of new reactions and catalysts , development of synthetic methods , new techniques for asymmetric synthesis , and determination of reaction mechanisms . The development of new chemistry using organometallic species is a rich and fertile area due to the unique ability of transition metal fragments to impart special reactivity, selectivity, and stability upon bonded organic moieties. Our research draws on these features to address problems in organic synthesis.

Organometallic Radical Reactions for Stereoselective Synthesis

Organometallic radical reactions are being investigated as new methods for carbon-carbon bond formation. By using transition metal fragments to template the reactions of organic moieties, control of chemoselectivity, regiochemistry and stereochemistry in radical cyclizations is feasible. A wide array of organometallic compounds are employed including iron olefin complexes, cobalt alkyne complexes, iron triene complexes, chromium carbene complexes and arene chromium complexes. The later are used for asymmetric synthesis where both enantiomers of a product are available from a single starting enantiomer. Applications of the newly developed methods to the syntheses of biologically active products such as antitumor agents, unnatural sugars, and antibiotics are under investigation.

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Honors & Awards

  • Richard Larock Research Lecture, University of California Davis, 2018
  • Leo and June Davis Frontiers Lecture, University of Iowa 2017
  • CSHEMA Innovation Award of Honor: Safety Training Consortium – UC Center for Laboratory Safety 2017
  • Outstanding Product Owner – UC Davis Information Technology Services, 2014
  • MERLOT Award for Exemplary Online Learning Resources, MERLOT Classics 2012
  • Hanson-Dow Award for Excellence in Teaching, 2010
  • StudySphere Award of Excellence, 2006
  • StudyWeb Excellence Award, 1999
  • Top 5% Chemistry Web Site, 1999
  • Alfred P. Sloan Research Fellowship, 1995-1997
  • Camille Dreyfus Teacher-Scholar Award, 1994-1999
  • National Science Foundation Young Investigator Award, 1992-1997

Representative Publications

Recent Publications

  • Sedef Karabiyikoglu, Byron A. Boon, and Craig A. Merlic. “Cycloaddition Reactions of Cobalt-Complexed Macrocyclic Alkynes: The Transannular Pauson–Khand Reaction.” J. Org. Chem., 2017, 82 (15), pp 7732–7744.  DOI: 10.1021/acs.joc.7b01369
  • Byron A. Boon, Aaron G. Green, Peng Liu, K. N. Houk, and Craig A. Merlic. “Using Ring Strain to Control 4 pi-Electrocyclization Reactions: Torquoselectivity in Ring Closing of Medium-Ring Dienes and Ring Opening of Bicyclic Cyclobutenes.” J. Org. Chem., 2017, 82 (9), pp 4613–4624.  DOI: 10.1021/acs.joc.7b00203
  • Cyndi Qixin He, Tiffany Q. Chen, Ashay Patel, Sedef Karabiyikoglu, Craig A. Merlic, and K. N. Houk. “Distortion, Tether, and Entropy Effects on Transannular Diels-Alder Cycloaddition Reactions of 10-18-Membered Rings.” J. Org. Chem., 2015, 80 (21), pp 11039–11047.  DOI: 10.1021/acs.joc.5b02288
  • Karabiyikoglu, Sedef; Iafe, Robert G.; Merlic, Craig A. “Ring-Closing Metathesis with Vicinal Dibromoalkenes as Protected Alkynes: A Synthetic Approach to Macrocyclic Enynes.” Org. Lett., 2015, 17 (21), pp 5248–5251.  DOI: 10.1021/acs.orglett.5b02595
  • Karabiyikoglu, Sedef; Merlic, Craig A. “Transannular [4+2] Cycloaddition Reactions of Cobalt-Complexed Macrocyclic Dienynes.” Org. Lett., 2015, 17 (16), pp 4086–4089.  DOI:10.1021/acs.orglett.5b01984
  • Green, Aaron G.; Liu, Peng; Merlic, Craig A.; and K. N. Houk. “Distortion/Interaction Analysis Reveals the Origins of Selectivities in Iridium-Catalyzed C-H Borylation of Substituted Arenes and 5-Membered Heterocycles.” J. Am. Chem. Soc., 2014, 136 (12), pp 4575–4583.  DOI: 10.1021/ja411699u
  • Iafe, R. G.; Kuo, J. L.; Hochstatter, D. G.; Saga, T. S.; Turner, J. W.; Merlic, C. A. “Increasing the Efficiency of the Transannular Diels-Alder Strategy via Palladium(II)-Catalyzed Macrocyclizations” Org. Lett., 2013, 15, 582-585. DOI: 10.1021/ol303394t.
  • Iafe, R. G.; Chan, D. G.; Kuo, J. L.; Boon, B. A.; Faizi, D. J.; Saga, T. S.; Turner, J. W.; Merlic, C. A. “Cyclization Strategies to Polyenes Using Pd(II)-Catalyzed Couplings of Pinacol Vinylboronates” Org. Lett., 2012, 14, 4282-4285. DOI: 10.1021/ol303394t
  • Chan, D. G.; Winternheimer, D. J.; Merlic, C. A. “Enol Silyl Ethers via Copper(II)-Catalyzed C-O Bond Formation” Org. Lett., 2011, 13, 2778-2781.  DOI: 10.1021/ol2009297
  • Winternheimer, D. J.; Shade, R. E.; Merlic, C. A. “Methods for Vinyl Ether Synthesis” Synthesis, 2010, 42, 2497-2511.  DOI: 10.1055/s-0030-1258166.
  • Winternheimer, D. J.; Merlic, C. A. “Alkoxydienes via Copper Promoted Couplings: Utilizing an Alkyne Effect” Org. Lett., 2010, 12, 2508-2510. DOI: 10.1021/ol100707s.
  • Shade, R. E.; Hyde, A. M.; Olsen, J.-C.; Merlic, C. A. “Copper-Promoted Coupling of Vinyl Boronates and Alcohols: A Mild Synthesis of Allyl Vinyl Ethers” J. Am. Chem. Soc., 2010, 132, 1202-1203.  DOI: 10.1021/ja907982w

Safety Publications

  • Schroeder, I.; Czornyj, E.; Blayney, M. B.; Wayne, N. L.; Merlic, C. A. “Proceedings of the 2018 Laboratory Safety Workshop: Hazard & Risk Management in the Laboratory” ACS Chem. Health Safety 2020, 27(2), 96-104. [link]
  • Svenningsen, G. S.; Williams, B.; Blayney, M. B.; Czornyj, E.; Schroeder, I.; Merlic, C. A. “Lessons Learned – Fluoride Exposure” ACS Chem. Health Safety 2020, 27(1), 40-42. [link]
  • Czornyj, E.; Schroeder, I.; Wayne, N. L.; Merlic, C. A. “Lessons Learned – Vacuum Pump Fire” J. Chem. Health Safety 2019, 26(6), 2. [link]
  • Czornyj, E.; Schroeder, I.; Wayne, N. L.; Merlic, C. A. “Lessons Learned – Mercury Thermometer Incident” J. Chem. Health Safety 2019, 26(4), 6-8. [link]
  • Czornyj, E.; Schroeder, I.; Wayne, N. L.; Merlic, C. A. “Organic Peroxide Incident” J. Chem. Health Safety 2019, 26(3), 3-4. [link]
  • Czornyj, E.; Newcomer, D.; Schroeder, I.; Wayne, N. L.; Merlic, C. A. “Proceedings of the 2016 Workshop Safety By Design – Improving Safety in Research Laboratories” J. Chem. Health Safety 2018, 25(4), 36-49. [link]
  • Merlic, C.; Ngai, E.; Schroeder, I.; Smith, K. “Report to the University of Hawaii at Manoa on the Hydrogen/Oxygen Explosion of March 16, 2016. Report 2: Recommendations for Improvements in UH Laboratory Safety Programs”  UC Center for Laboratory Safety, 2016.  [link]
  • Merlic, C.; Ngai, E.; Schroeder, L.; Smith, K. “Report to the University of Hawaii at Manoa on the Hydrogen/Oxygen Explosion of March 16, 2016. Report 1: Technical Analysis of Accident” UC Center for Laboratory Safety, 2016. [link]

Previous Publications

  • Garcia, Y.; Schoenebeck, F.; Legault, C. Y.; Merlic, C. A.; Houk, K. N. “Theoretical Bond Dissociation Energies of Halo-Heterocycles: Trends and Relationships to Regioselectivity in Palladium-Catalyzed Cross Coupling Reactions” J. Am. Chem. Soc., 2009, 131, 6632-6639. [link]
  • Legault, C. Y.; Garcia, Y.; Merlic, C. A.; Houk, K. N. “Origin of Regioselectivity in Palladium Catalyzed Cross-Coupling Reactions of Heterocycles” J. Am. Chem. Soc., 2007, 129, 12664-12665. [link]
  • Yu, W.; Zhang, F.; Zamborszky, F.; Alavi, B.; Baur, A.; Merlic, C. A.; Brown, S. E. “Electron-Lattice Coupling and Broken Symmetries of the Molecular Salt (TMTTF)2SbF6” Physical Review B. 2004, 70 (12), 121101-1—121101-4. [link]
  • Hietbrink, B. N.; Tantillo, D. J.; Houk, K. N.; Merlic, C. A. “Chromium Tricarbonyl Coordinated Carbocations” In Carbocation Chemistry; Olah, G. A; Prakash, G. K. S., Eds.; Wiley: New York, 2004; Chapter 10, pp. 279-290. [BOOK CHAPTER] [link]
  • Yu, W.; Zamborszky, F.; Alavi, B.; Baur, A.; Merlic, C. A.; Brown, S. E. “Influence of charge order on the ground states of TMTTF molecular salts” Journal de Physique IV 2004, 114, 35-40. [link]
  • Shelkovnikov, S.; Merlic, C. A.; Gonick, H. C. “Influence of Nitric Oxide Donors and Peroxynitrite on the Contractile Effect and Concentration of Norepinephrine” Life Sciences, 2004, 74, 2919-2928. [link]
  • Lima, M. A.; Barbosa-Filho, J. M.; Merlic, C. A.; Doroh, B. C.; Maia, J. G. S.; Silva, M. S.; da-Cunha, E. V. L. “Alkaloids and volatile constituents from Guatteria poepigiana” Biochemical Systematics and Ecology 2004, 32, 347-349. [link]
  • Merlic, C. A.; Doroh, B. C. “Amine Catalyzed Coupling of Aldehydes and Ketenes Derived from Fischer Carbene Complexes: Formation of b-Lactones and Enol Ethers” J. Org. Chem. 2003, 68, 6056-6059. [link]
  • Merlic, C. A.; Zechman, A. L. “Selectivity in Rhodium(II) Catalyzed Reactions of Diazo Compounds: Effects of Catalyst Electrophilicity, Diazo Substitution, and Substrate Substitution. From Chemoselectivity to Enantioselectivity” Synthesis 2003, 1137-1156. [REVIEW] [link]
  • Zamborszky, F.; Yu, W.; Raas, W.; Brown, S. E.; Alavi, B.; Merlic, C. A.; Baur, A.; Lefebvre, S.; Wzietek, P.; “Influence of Charge Order on the Ground State of TMTTF Conductors” Journal de Physique IV 2002, 12, 139-144.
  • Zamborszky, F.; Yu, W.; Raas, W.; Brown, S. E.; Alavi, B.; Merlic, C. A.; Baur, A.; “Competition and Coexistence of Bond and Charge Orders in (TMTTF)2AsF6” Physical Review B. 2002, 66 (8), 081103-1—081103-4.
  • Merlic, C. A.; Zechman, A. L.; Miller, M.; “Reactivity of (h6-Arene)tricarbonylchromium Complexes with Carbenoids: Arene Activation or Protection?” J. Am. Chem. Soc. 2001, 123, 11101-11102. [link]
  • Merlic, C. A.; Hietbrink, B. N.; Houk, K. N.; “Donor and Acceptor Properties of the Chromium Tricarbonyl Substituent in Benzylic and Homobenzylic Anions, Cations, and Radicals” J. Org. Chem. 2001, 66, 6738-6744. [link]
  • Merlic, C. A.; You, Y.; McInnes, D. M.; Zechman, A. L.; Miller, M. M.; Deng, Q. “Benzannulation Reactions of Fischer Carbene Complexes for the Synthesis of Indolocarbazoles” Tetrahedron 2001, 57, 5199-5212. [link]
  • Merlic, C. A.; Miller, M.; Hietbrink, B. N.; Houk, K. N.; “Reactivity of (h6-Arene)tricarbonylchromiumComplexes Toward Additions of Anions, Cations, and Radicals” J. Am. Chem. Soc. 2001, 123, 4904-4918. [link]
  • Merlic, C. A.; Walsh, J. “The Tricarbonylchromium Template for Stereocontrol in Radical Reactions of Arenes” J. Org. Chem. 2001, 66, 2265-2274. [link]
  • Merlic, C. A.; Aldrich, C. C. Albaneze-Walker, J.; Saghatelian, A.; Mammen, J. “Total Synthesis of the Calphostins: Application of Fischer Carbene Complexes and Thermodynamic Control of Atropisomers” J. Org. Chem. 2001, 66, 1297-1309. [link]
  • Merlic, C. A.; Miller, M. “Neighboring Group Participation by Chromium in Substitution Reactions of (h6-Arene)tricarbonylchromium Complexes” Organometallics 2001, 20, 373-375. [link]
  • Merlic, C. A.; Fam, B. C.; Miller, M. M. “WebSpectra: Online NMR and IR Spectra for Students” J. Chem. Ed. 2001, 78, 118-120. [link]
  • Chow, D. S.; Zamborszky, F.; Alavi, B.; Tantillo, D. J.; Baur, A.; Merlic, C. A.; Brown, S. E. “Charge Ordering in the TMTTF Family of Molecular Conductors” Phys. Rev. Lett. 2000, 85, 1698-1701. [link]
  • Merlic, C. A.; Baur, A.; Aldrich, C. C. “Acylamino Chromium Carbene Complexes: Direct Carbonyl Insertion, Formation of Münchnones and Trapping with Dipolarophiles”J. Am. Chem. Soc. 2000, 122, 7398-7399. [link]
  • Tantillo, D. J.; Hietbrink, B. N.; Merlic, C. A.; Houk, K. N. “Attenuating and Supplanting Nonclassical Stabilization: Cr(CO)3-Complexed Benzonorbornenyl Cations” J. Am. Chem. Soc. 2000, 122, 7136-7137. [link]
  • Merlic, C. A.; Baur, A.; Yamada, K.; Brown, S. E. “Synthesis of Quadruply Carbon-13 Labeled Tetramethyltetrathiafulvalene ” Syn. Commun. 2000, 30, 2677-2685. [link]
  • Merlic, C. A.; Aldrich, C. C.; Albaneze-Walker, J.; Saghatelian, A. “Carbene Complexes in the Synthesis of Complex Natural Products: Total Synthesis of the Calphostins” J. Am. Chem. Soc. 2000, 122, 3224-3225. [link]
  • Chow, D. S.; Brown, S. E.; Wzietek, P.; Fogliatti, D.; Alavi, B.; Merlic, C. “Singular Behavior in the Pressure-Tuned Competition Between Spin-Peierls and Antiferromagnetic Ground States of (TMTTF)2PF6” Synthetic Metals 1999, 103, 2058-2059. [link]
  • Brown, S. E.; Clark, W. G.; Alavi, B.; Chow, D. S.; Merlic, C. A.; Tantillo, D.J. “Incommensurate Phase of the Organic Spin-Peierls Compound (TMTTF)2PF6” Synthetic Metals, 1999, 103, 2056-2057. [link]
  • Merlic, C. A.; Baur, A.; Tantillo, D. J.; Brown, S. E. “Synthesis of Carbon-13 Labeled Tetramethyltetrathiafulvalene” Syn. Commun. 1999, 29, 2953-2958. [link]
  • Brown, S. E.; Clark, W. G.; Alavi, B.; Hall, D.; Naughton, M. J.; Tantillo, D. J.; Merlic, C. A. “High- Field Magnetization of the Spin-Peierls Compound (TMTTF)2PF6” Phys. Rev. B 1999, 60, 6270-6272.
  • Merlic, C. A.; Walsh, J. C.; Tantillo, D. J.; Houk, K. N. “Chemical Hermaphroditism: The Potential of the Cr(CO)3 Moiety to Stabilize Transition States and Intermediates with Anionic, Cationic, or Radical Character at the Benzylic Position” J. Am. Chem. Soc. 1999, 121, 3596-3606. [link]
  • Chow, D. S.; Wzietek, P.; Fogliatti, D.; Alavi, B.; Tantillo, D. J.; Merlic, C. A.; Brown, S. E “Singular Behavior in the Pressure-Tuned Competition Between Spin-Peierls and Antiferromagnetic States of (TMTTF)2PF6” Phys. Rev. Lett. 1998, 81, 3984-3987.[link]
  • Brown, S. E.; Clark, W. G.; Zamborszky, F.; Klemme, B. J.; Kriza, G.; Alavi, B.; Merlic, C. A.; Tantillo, D. J.; Kuhns, P.; Moulton, W. “13C NMR Measurements of the High-Magnetic Field, Low-temperature Phases of (TMTTF)2PF6” Phys. Rev. Lett. 1998, 80, 5429-5432. [link]
  • Merlic, C. A.; Walsh, J. C. “Completely Diastereoselective Radical Reactions Using Arenechromium Tricarbonyl Complexes” Tetrahedron Lett. 1998, 39, 2083-2086. [link]
  • Merlic, C. A.; Wu, F. “Synthesis of b-Keto Fischer Carbene Complexes” Journal of Organometallic Chemistry 1998, 553, 183-191. [link]
  • Zwick, F.; Brown, S.; Margaritondo, G.; Merlic, C.; Onellion, M.; Voit, J.; Grion, M. “Absence of Quasiparticles in the Photoemission Spectra of Quasi-One-Dimensional Bechgaard Salts” Phys. Rev. Lett. 1997, 79, 3982-3985. [link]
  • Merlic, C. A.; McInnes, D. M. “Synthesis of Indolocarbazoles via Sequential Palladium Catalyzed Cross Coupling and Benzannulation Reactions” Tetrahedron Lett. 1997, 38, 7661-7664. [link]
  • Merlic, C. A.; McInnes, D. M.; You, Y. “Synthesis of Indolocarbazoles via Annulations of Chromium Carbene Complexes” Tetrahedron Lett. 1997, 38, 6787-6790. [link]
  • Merlic, C. A.; Walker, M. J. “Virtual Office Hours: Facilitating Faculty-Student Communication” Int. J. Educ. Telecommun. 1997, 3, 261-278.
  • Merlic, C. A.; Pauly, M. E. “Ruthenium-Catalyzed Cyclizations of Dienylalkynes Via Vinylidene Intermediates” J. Am. Chem. Soc. 1996, 118, 11319-11320. [link]
  • Merlic, C. A.; Walker, M. J. “Virtual Office Hours: A Communication Tool for Students and Teachers” WebNet 96 World Conference of the Web Society Preceedings, Maurer, Ed., 1996, Association for the Advancement of Computing in Education, pp 360-365.
  • Merlic, C. A.; Motamed, S.; Quinn, B. “Structure Determination and Synthesis of Fluoro Nissl Green: An RNA Binding Fluorochrome” J. Org. Chem. 1995, 60, 3365-3369. [link]
  • Merlic, C. A.; Albaneze, J. “Synthesis of Alkoxy-Substituted Allenyl- and Propargylstannane Reagents from Carbene Complexes” Tetrahedron Lett. 1995, 36, 1011-1014. [link]
  • Merlic, C. A.; Albaneze, J. “Rapid Synthesis of Functionalized, Alkoxy-Substituted, Allylstannanes from Carbene Complexes” Tetrahedron Lett. 1995, 36, 1007-1010. [link]
  • Quinn, B; Toga, A.; Motamed, S.; Merlic, C. A.. “Fluoro Nissl Green: A Novel Fluorescent Counterstain for Neuroanatomy” Neuroscience Lett. 1995, 184, 169-172. [link]
  • Merlic, C. A.; Bendorf, H. D. “Cyclopropanation of C60 Via a Fischer Carbene Complex” Tetrahedron Lett. 1994, 35, 9529-9532. [link]
  • Merlic, C. A. “2-Hydroxy-1-methoxy-furo[2,3-b]naphthalene” In Photochemical Key Steps in Organic Synthesis; Mattay, J.; Griesbeck, A., Eds.; VCH: Weinheim, Germany, 1994, pp 271-273.
  • Merlic, C. A.; Roberts, W. M. “Regioselectivity of Photochemical Annulations of Chromium Carbene Complexes” Tetrahedron Lett. 1993, 34, 7379-7382. [link]
  • Merlic, C. A.; Burns, E. E. “Chemoselectivity in the Isonitrile Metathesis Route to Aromatic Amines” Tetrahedron Lett. 1993, 34, 5401-5404. [link]
  • Merlic, C. A.; Bendorf, H. D. “Titanium-Templated [4+2] Oxidative Cycloadditions: A Facile Route to 7-Hydroxynorbornenes”Organometallics 1993, 12, 559-564. [link]
  • Merlic, C. A.; Xu, D; Gladstone, B. “Aminobenzannulation Via Photocyclization Reactions of Chromium Dienyl(Amino)carbene Complexes. Synthesis of Ortho Amino Aromatic Alcohols” J. Org. Chem. 1993, 58, 538-545. [link]
  • Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. ” Stereochemistry of Intermolecular Radical Reactions of Unsaturated Tungsten Carbene Complexes,” Tetrahedron Lett. 1993, 34, 227-230. [link]
  • Merlic, C. A.; Burns, E. E.; Xu, D.; Chen, S. Y. “Aminobenzannulation Via Metathesis of Isonitriles Using Chromium Carbene Complexes” J. Am. Chem. Soc. 1992, 114, 8722-8724. [link]
  • Merlic, C. A.; Adams, B. “Molybdenum-95 Nuclear Magnetic Resonance Studies on Molybdenum Carbonyl Complexes of Isonitriles and Amines” J. Organomet. Chem. 1992, 431, 313-325. [link]
  • Merlic, C. A.; Xu, D.; Khan, S. I. ” Synthesis, Structure and Reactivity of Cyclic Arene Chromium Carbene Complexes” Organometallics 1992, 11, 412-418. [link]
  • Merlic, C.A.; Xu, D. “Intermolecular Radical Reactions of Unsaturated Chromium and Tungsten Carbene Complexes,” J. Am. Chem. Soc. 1991, 113, 9855-9856. [link]
  • Merlic, C.A.; Xu, D. “Cyclization Reactions of Dienyl Chromium Carbene Complexes. Entry to Ortho Substituted Aromatic Alcohols via a Designed Photoreaction” J. Am. Chem. Soc. 1991, 113, 7418-7420. [link]
  • Merlic, C.A.; Semmelhack, M.F. “An Interesting Chloride Ion Effect in the Heck Reaction,” J. Organomet. Chem. 1990, 391, C23-C27. [link]
  • Trost, B.M.; Merlic, C.A. “Ligand Dependence of Molybdenum Catalyzed Alkylations. Molybdenum Isonitrile Complexes as a New Class of Highly Reactive Alkylation Catalysts,” J. Am. Chem. Soc. 1990, 112, 9590-9600. [link]
  • Trost, B.M.; Merlic, C.A. “Geminal Alkylation – Substitutions of Allyl Sulfones. Regiocontrol via Molybdenum Catalysis,” J. Org. Chem. 1990, 55, 1127-1129. [link]
  • Trost, B.M.; Merlic, C.A. “Diastereoselectivity Control Elements. Acyclic Diastereocontrol in Formation and Reactions of g-hydroxysulfones,” J. Am. Chem. Soc. 1988, 110, 5216-5218. [link]
  • Little, R.D.; Losinski-Dang, L.; Venegas, M.G.; Merlic, C.A. “Some Unusual Reactions of Molecular Oxygen with Bicyclic Diazenes which Typically Serve as Precursors to Alkylidenecyclopentane-1,3-diyls; Peroxide Formation,” Tetrahedron Lett. 1983, 24, 4499-4502. [link]