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THIOUREA-CATALYZED NUCLEOPHILIC DESYMMETRIZATION OF MESO-CYCLOPROPANES

Award Number: F32GM082063
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: FELLOWSHIP/SCHOLARSHIP/STUDENT LOANS
PERIOD OF PERFORMANCE START DATE: 09/01/2007
PERIOD OF PERFORMANCE END DATE: 08/31/2009

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THIOUREA-CATALYZED NUCLEOPHILIC DESYMMETRIZATION OF MESO-CYCLOPROPANES - DESCRIPTION (provided by applicant): Asymmetric catalysis provides necessary synthetic tools for the synthesis of enantiomerically pure, biologically active molecules. The field of asymmetric catalysis has been dominated by the use of transition metal complexes. The use of transition metal catalyzed reactions poses grave concerns for the chemical and pharmaceutical industry. Great care must be taken in purification and disposal practices associated with the use of transition metal catalysts, as many of these complexes are toxic. To develop alternatives to these practices, chemists have turned to nature for inspiration in the development of more efficient, selective, and environmentally benign catalysts for useful organic transformations. With an increase in the understanding of the mechanisms behind enzyme function, interest has erupted over the last decade in the use of organic molecules as catalysts for asymmetric organic transformations. The absence of metals at the active site of many enzymes demonstrates the ability of non-metallic functional groups to serve as catalytic centers. Chemists are attempting to mimic these non-metallic active sites with small organic compounds. This proposal outlines the development of stereoselective 1,5-functionalization of carbonyls through thiourea catalyzed desymmetrizations of meso-cyclopropanes by nucleophilic ring opening. Current synthetic methodologies allow for the facile construction of meso-cyclopropanes and their desymmetrization would give rise to complex chiral scaffold. The bifunctional nature of the thiourea catalysts should result in simultaneous activation of the cyclopropane as well as the nucleophile. The goal of this research is to develop thiourea compounds as catalysts for this transformation.


Issue Date FY	Funding FY	Legal Entity Name	Legal Entity Address	Legal Entity City	Legal Entity State	Legal Entity Zip Code	Legal Entity COUNTY	Legal Entity COUNTRY	Assistance Listing	Award Code	Budget Year	Action Date	Action Type	Action Amount

Issue Date FY: 2008 ( Subtotal = $46,826 )
2008	2008	HARVARD UNIVERSITY PRESIDENT & FELLOWS	HOLYOKE 466, 1350 MASS AVENUE	CAMBRIDGE	MA	02138	MIDDLESEX	USA	Biomedical Research and Research Training	000	2	8/29/2008	NON-COMPETING CONTINUATION	$46,826
														Subtotal = $46,826

Issue Date FY: 2007 ( Subtotal = $44,846 )
2007	2007	HARVARD UNIVERSITY PRESIDENT & FELLOWS	HOLYOKE 466, 1350 MASS AVENUE	CAMBRIDGE	MA	02138	MIDDLESEX	USA	Biomedical Research and Research Training	000	1	8/9/2007	NEW	$44,846
														Subtotal = $44,846

Grand Total All Awards = $91,672

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THIOUREA-CATALYZED NUCLEOPHILIC DESYMMETRIZATION OF MESO-CYCLOPROPANES

Award Number: F32GM082063

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

AWARD ACTIVITY TYPE: FELLOWSHIP/SCHOLARSHIP/STUDENT LOANS

PERIOD OF PERFORMANCE START DATE: 09/01/2007

PERIOD OF PERFORMANCE END DATE: 08/31/2009

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