) The long-term goal of this research program is to develop efficient, reliable and practical catalytic asymmetric reactions, which will provide synthetic chemists in both academia and industry with the necessary tools to design efficient, practical and environmentally friendly routes for the synthesis of pharmaceuticals and other biologically active compounds. We strive to achieve this goal through the discovery and development of readily accessible chiral catalysts and a broad exploration of their ability to promote catalytic asymmetric reactions. Specifically we will focus on the development of readily available chiral Lewis base catalysts for a wide range of asymmetric nucleophile-electrophile reactions via an approach that combines extensive reaction screening, intensive development and optimization of reaction conditions, and thoughtful mechanistic and structural studies. To illustratethe potential usefulness of these asymmetric reactions in biomedical research, we outline synthetic routes which utilize these asymmetric reactions to transform readily available prochiral precursors into various optically active chiral building blocks for asymmetric synthesis of biologically interesting compounds.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM061591-04
Application #
6729039
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Schwab, John M
Project Start
2001-04-01
Project End
2006-03-31
Budget Start
2004-04-01
Budget End
2005-03-31
Support Year
4
Fiscal Year
2004
Total Cost
$230,563
Indirect Cost
Name
Brandeis University
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
616845814
City
Waltham
State
MA
Country
United States
Zip Code
02454
Li, Zhe; Hu, Bin; Wu, Yongwei et al. (2018) Control of chemoselectivity in asymmetric tandem reactions: Direct synthesis of chiral amines bearing nonadjacent stereocenters. Proc Natl Acad Sci U S A 115:1730-1735
Zhou, Xiao; Wu, Yongwei; Deng, Li (2016) Cinchonium Betaines as Efficient Catalysts for Asymmetric Proton Transfer Catalysis: The Development of a Practical Enantioselective Isomerization of Trifluoromethyl Imines. J Am Chem Soc 138:12297-302
Hu, Lin; Wu, Yongwei; Li, Zhe et al. (2016) Catalytic Asymmetric Synthesis of Chiral ?-Amino Ketones via Umpolung Reactions of Imines. J Am Chem Soc 138:15817-15820
Hu, Lin; Lu, Xiaojie; Deng, Li (2015) Catalytic Enantioselective Peroxidation of ?,?-Unsaturated Aldehydes for the Asymmetric Synthesis of Biologically Important Chiral Endoperoxides. J Am Chem Soc 137:8400-3
Zheng, Yang; Deng, Li (2015) Catalytic Asymmetric Direct Aldol Reaction of ?-Alkyl Azlactones and Aliphatic Aldehydes. Chem Sci 6:6510-6514
Wu, Yongwei; Hu, Lin; Li, Zhe et al. (2015) Catalytic asymmetric umpolung reactions of imines. Nature 523:445-50
Lu, Xiaojie; Deng, Li (2014) Catalytic asymmetric peroxidation of ?,?-unsaturated nitroalkenes by a bifunctional organic catalyst. Org Lett 16:2358-61
Wu, Yongwei; Deng, Li (2012) Asymmetric synthesis of trifluoromethylated amines via catalytic enantioselective isomerization of imines. J Am Chem Soc 134:14334-7
Lee, Jung Hwa; Deng, Li (2012) Asymmetric approach toward chiral cyclohex-2-enones from anisoles via an enantioselective isomerization by a new chiral diamine catalyst. J Am Chem Soc 134:18209-12
Provencher, Brian A; Bartelson, Keith J; Liu, Yan et al. (2011) Structural study-guided development of versatile phase-transfer catalysts for asymmetric conjugate additions of cyanide. Angew Chem Int Ed Engl 50:10565-9

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