Coltart, Don - University of Houston - Department of Chemistry

个人简介

Postdoctoral Fellow, Memorial Sloan-Kettering Cancer Center Ph.D., University of Alberta, 2000 M.Sc., University of Manitoba, 1995 B.Sc., University of Manibota, 1993

研究领域

Synthetic organic chemistry is the unifying feature of all research in the Coltart group. We are particularly interested in the development of new synthetic methods and the use of those methods to enable the total synthesis of structurally complex, biologically active natural products. The methodology research in our group focuses mainly on asymmetric carbon–carbon bond formation, especially the α-alkylation of carbonyl compounds. We have been developing two programs in parallel along these lines. One is based on the use of activated hydrazones and centers around achieving the longstanding, yet unrealized goal of developing a general approach to the asymmetric a-alkylation of ketones. The second focuses on soft enolization of thioesters as a mild and operationally simple alternative to conventional hard enolization procedures. Activated Hydrazones and Oximes in the Development of New Asymmetric Methods A major aspect of our current research effort is the study of activated hydrazones, oximes, and related compounds in the development of new asymmetric methods. The methods we are developing may be categorized according to two broad reaction manifolds: 1) those based on nucleophilic addition to N-sulfonyl azoalkenes, nitrosoalkenes, and related compounds and 2) those based on electrophilic addition to azaenolate mono- or dianions. Direct Carbon–Carbon Bond Formation via Soft Enolization of Thioesters One of our primary research objectives is the development of mild and operationally simple approaches to key carbon–carbon bond-forming reactions. In terms of developing mild synthetic methods, Nature’s repertoire of reactions is an ideal source of inspiration given that these reactions are conducted in an aqueous environment and, typically, under aerobic conditions. Moreover, years of evolution have led to the refinement of these transformations and much can be learned from the manner in which they are conducted. Inspired by the way in which carbon–carbon bond formation occurs in citrate synthase, we have been studying the soft enolization of thioesters as a means of developing simple approaches to certain fundamental organic transformations. Natural Products Total Synthesis Much of the methodology that we have developed has been, or is being applied in the context of natural product total synthesis. Often the final objective is not the synthesis of the natural product, which itself is a worthwhile and challenging goal. Instead, the completed synthesis marks the transition into biological investigations.

近期论文

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Catalytic Asymmetric Addition of Thiols to Nitrosoalkenes: An Umpolung Strategy for the Synthesis of Chiral Non-Racemic α-Sulfenyl Ketones. Hatcher, J. M.; Kohler, M. C.; Coltart, D. M. Org. Lett. 2011, 13, 3810–3813. Asymmetric Total Synthesis of the Anti-Malarial Drug (+)-Mefloquine Hydrochloride via Chiral N-Amino Cyclic Carbamate Hydrazones. Knight, J. D.; Sauer, S. J.; Coltart, D. M. Org. Lett. 2011, 13, 3118–3121. Regioselective Asymmetric a,α-Bisalkylation of Ketones via Complex Induced Syn-Deprotonation. Wengryniuk, S. E.; Lim, D.; Coltart, D. M. J. Am. Chem Soc. 2011, 133, 8714–8720. Asymmetric Total Synthesis of (+)- and (–)-Clusianone and (+)- and (–)-Clusianone Methyl Enol Ether via ACC Alkylation and Evaluation of their Anti-HIV Activity. Garnsey, M. R.; Matous, J. A.; Kwiek, J. J.; Coltart, D. M. Bioorg. Med. Chem. Lett. 2011, 21, 2406–2409. Direct Carbon–Carbon Bond Formation via Soft Enolization: Aldol Addition of α-Halogenated Thioesters. Yost, J. M.; Alfie, R.; Tarsis, E. T.; Coltart, D. M. Chem. Commun. 2011, 47, 571–572. The Origins of Stereoselectivity in the α-Alkylation of Chiral Hydrazones. Krenske, E. H.; Houk, K. N.; Lim, D.; Wengryniuk, S. E.; Coltart, D. M. J. Org. Chem. 2010, 75, 8578–8584. Development of a Strategy for the Asymmetric Synthesis of Polycyclic Polyprenylated Acylphloroglucinols via N-Amino Cyclic Carbamate Hydrazones: Application to the Total Synthesis of (+)-Clusianone. Garnsey, M. R.; Lim, D.; Yost, J. M.; Coltart, D. M. Org. Lett. 2010, 12, 5234-5237. Direct Carbon–Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled Syn-Aldol Addition of α-Halo Thioesters. Sauer, S. J.; Garnsey, M. R.; Coltart, D. M. J. Am. Chem. Soc. 2010, 132, 13997–13999. Direct Carbon–Carbon Bond Formation via Soft Enolization: A Biomimetic Asymmetric Mannich Reaction of Phenylacetate Thioesters. Kohler, M. C; Yost, J. M.; Garnsey, M. R.; Coltart, D. M. Org. Lett. 2010, 12, 3376–3379. Copper-(I) Catalyzed Addition of Grignard Reagents to In Situ-Derived N-Sulfonyl Azoalkenes: An Alkylation Procedure Applicable to the Formation of up to Three Contiguous Quaternary Centers. Hatcher, J. M.; Coltart, D. M. J. Am. Chem. Soc. 2010, 132, 4546–4547. A Practical Synthesis of β-Keto Thioesters via Direct Crossed-Claisen Coupling of Thioesters and N-Acylbenzotriazoles. Zhou, G.; Lim, D.; Coltart, D. M. Synthesis 2009, 3350–3352. Direct Carbon–Carbon Bond Formation via Soft Enolization of Thioesters: An Operationally Simple Mannich Addition Reaction. Yost, J. M.; Garnsey, M. R.; Kohler, M. C.; Coltart, D. M. Synthesis, 2009, 56–58. Overcoming the Limitations of the Baylis-Hillman Reaction: A Rapid and General Synthesis of α-Alkenyl β-Hydroxy Thioesters. Tarsis, E. T.; Gromova, A.; Lim, D.; Zhou, G.; Coltart, D. M. Org. Lett. 2008, 10, 4819–4822. Direct Carbon–Carbon Bond Formation via Chemoselective Soft Enolization of Thioesters: A Remarkably Simple and Versatile Crossed-Claisen Reaction Applied to the Synthesis of LY294002. Zhou, G.; Lim, D.; Coltart, D. M. Org. Lett. 2008, 10, 3809–3812. Simple and Efficient Asymmetric α-Alkylation and a,α-Bisalkylation of Acyclic Ketones Using Chiral N-Amino Cyclic Carbamate Hydrazones. Lim, D.; Coltart, D. M. Angew. Chem. Int. Ed. 2008, 47, 5207–5210. MgBr2-OEt2 - Promoted Coupling of Ketones and Activated Acyl Donors via Soft Enolization: A Practical Synthesis of 1,3-Diketones. Lim, D.; Zhou, G.; Livanos, A. E.; Fang, F.; Coltart, D. M. Synthesis, 2008, 2148–2152. A Facile and Efficient Anti-Selective Four-Component Direct Aldol Addition via Chemoselective Thioester Enolate Formation. Zhou, G.; Yost, J. M.; Sauer, S.; Coltart, D. M. Org. Lett. 2007, 9, 4663–4665. Direct Carbon–Carbon Bond Formation via Soft Enolization: A Facile and Efficient Synthesis of 1,3-Diketones. Lim, D.; Fang, F.; Zhou, G.; Coltart, D. M. Org. Lett. 2007, 9, 4139–4142. A Direct Aldol Addition of Simple Thioesters Employing Soft Enolization. Zhou, G.; Yost, J. M.; Coltart, D. M. Synthesis 2007, 478–482. A Facile and Efficient Direct Aldol Addition of Simple Thioesters. Yost, J. M.; Zhou, G.; Coltart, D. M. Org. Lett. 2006, 8, 1503–1506. "