New asymmetric epoxidation reactions enabled by chiral metalbishydroxamic acid catalysts.

Saved in:

Bibliographic Details
Author / Creator:	Li, Zhi.
Imprint:	2011.
Description:	130 p.
Language:	English
Format:	E-Resource Dissertations
Local Note:	School code: 0330.
URL for this record:	http://pi.lib.uchicago.edu/1001/cat/bib/8855420

Hidden Bibliographic Details
Other authors / contributors:	University of Chicago.
ISBN:	9781124717876
Notes:	Advisor: Hisashi Yamamoto. Thesis (Ph.D.)--The University of Chicago, Division of the Physical Sciences, Department of Chemistry, 2011. Dissertation Abstracts International, Volume: 72-09, Section: B, page: 5313.
Summary:	Chiral C2-symmstric bishydroxamic acid ligands were applied to the vanadium-catalyzed asymmetric desymmetrization epoxidation of meso-secondary allylic and homoallylic alcohols to provide excellent stereoselectivies. New chiral metal catalyst systems utilizing zirconium or hafnium as metal and bishydroxamic acids as chiral ligands were discovered. They could be applied to the highly enantioselective epoxidation of homoallylic and bishomoallylic alcohols. These new reactions featured high enantioselectivity and high efficiency for gem-disubstituted homoallylic and bishomoallylic substrates and Z-substituted homoallylic alcohols. Nucleophilic additives were shown to improve the reaction efficiency. The mechanism and stereochemical induction rules of these reactions were discussed by comparing with the vanadium-based catalysts.

Similar Items