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 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 #
5R01GM059705-02
Application #
6182035
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Schwab, John M
Project Start
1999-08-01
Project End
2003-07-31
Budget Start
2000-08-01
Budget End
2001-07-31
Support Year
2
Fiscal Year
2000
Total Cost
$225,127
Indirect Cost

  Institution

Name
Colorado State University-Fort Collins
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
112617480
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