Several investigations into regio-, diastereo-, and enantioselective transformations of zirconocene imido complexes and their products have been proposed (2+2) cycloaddition of allylimido zirconium complexes with allenes and/or alkynes, followed by (3,3) sigmatropic rearrangement, has the potential for highly regio- and diastereoselective functionalization of simple organic compounds. The overall process is the formal addition of amino and allyl groups across a carbon-carbon multiple bond. Subsequent functionalization or rearrangement would yield an array of complex organic products from simple starting materials. An enantioselective desymmetrization of meso epoxides and/or aziridines is also described that would result in production of chiral allyl alcohols and amines or chiral amino alcohols and diamines. Finally, mechanistic determination of the electronic influence of the metallocene and the nitrogen substituents of zirconocene imido complexes on the (2+2) cycloaddition reaction with simple alkenes will shed light on the origin of the high reactivity of this system and possibly elucidate methods for enhancing or tuning that reactivity.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Postdoctoral Individual National Research Service Award (F32)
Project #
1F32GM064940-01
Application #
6445270
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Ikeda, Richard A
Project Start
2002-01-21
Project End
Budget Start
2002-01-21
Budget End
2003-01-20
Support Year
1
Fiscal Year
2002
Total Cost
$36,592
Indirect Cost
Name
University of California Berkeley
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
094878337
City
Berkeley
State
CA
Country
United States
Zip Code
94704