Abstract

The overall goal of the proposed research is to explore the mechanistic features and synthetic potential of chiral dioxiranes.
The specific aims of the proposed research are: (1) to understand the mechanism and transition states involved in asymmetric epoxidation of olefins by chiral dioxiranes; (2) to further design and search for new ketone catalysts with high stability, reactivity, and enantioselectivity; (3) to explore and expand the scope of dioxirane-mediated asymmetric epoxidation; (4) to apply the newly developed asymmetric epoxidation to the synthesis of useful chiral building blocks and biologically active compounds. ? ?

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM059705-06
Application #
6755182
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Schwab, John M
Project Start
1999-08-01
Project End
2007-07-31
Budget Start
2004-08-01
Budget End
2005-07-31
Support Year
6
Fiscal Year
2004
Total Cost
$308,407
Indirect Cost

  Institution

Name
Colorado State University-Fort Collins
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
785979618
City
Fort Collins
State
CO
Country
United States
Zip Code
80523

  Publications

Wong, O Andrea; Shi, Yian (2009) Asymmetric epoxidation of fluoroolefins by chiral dioxirane. Fluorine effect on enantioselectivity. J Org Chem 74:8377-80
Wong, O Andrea; Wang, Bin; Zhao, Mei-Xin et al. (2009) Asymmetric epoxidation catalyzed by alpha,alpha-dimethylmorpholinone ketone. Methyl group effect on spiro and planar transition states. J Org Chem 74:6335-8
Wang, Bin; Wu, Xin-Yan; Wong, O Andrea et al. (2009) A diacetate ketone-catalyzed asymmetric epoxidation of olefins. J Org Chem 74:3986-9
Burke, Christopher P; Shi, Yian (2009) Enantioselective epoxidation of nonconjugated cis-olefins by chiral dioxirane. Org Lett 11:5150-3
Wang, Bin; Wong, O Andrea; Zhao, Mei-Xin et al. (2008) Asymmetric epoxidation of 1,1-disubstituted terminal olefins by chiral dioxirane via a planar-like transition state. J Org Chem 73:9539-43
Burke, Christopher P; Shu, Lianhe; Shi, Yian (2007) An N-aryl-substituted oxazolidinone-containing ketone-catalyzed asymmetric epoxidation with hydrogen peroxide as the primary oxidant. J Org Chem 72:6320-3
Burke, Christopher P; Shi, Yian (2007) Enantioselective epoxidation of conjugated cis-enynes by chiral dioxirane. J Org Chem 72:4093-7
Shen, Yu-Mei; Wang, Bin; Shi, Yian (2006) Enantioselective synthesis of 2-aryl cyclopentanones by asymmetric epoxidation and epoxide rearrangement. Angew Chem Int Ed Engl 45:1429-32
Goeddel, David; Shu, Lianhe; Yuan, Yi et al. (2006) Effective asymmetric epoxidation of styrenes by chiral dioxirane. J Org Chem 71:1715-7
Burke, Christopher P; Shi, Yian (2006) Regio- and enantioselective epoxidation of dienes by a chiral dioxirane: synthesis of optically active vinyl cis-epoxides. Angew Chem Int Ed Engl 45:4475-8

Showing the most recent 10 out of 25 publications