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Synlett 2005(7): 1047-1072
DOI: 10.1055/s-2005-865214
DOI: 10.1055/s-2005-865214
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Chiral-Auxiliary-Controlled Diastereoselective Epoxidations
Further Information
Received
13 December 2004
Publication Date:
14 April 2005 (online)
Publication History
Publication Date:
14 April 2005 (online)
Abstract
An overview of the literature through May 2004 on the available chiral auxiliaries for stereoselective epoxidation is reviewed, with emphasis on synthetic utility. The mechanistic complexities of the π-facial selectivity are scrutinized and plausible transition structures for the oxygen-transfer process are proposed. Convenient methods for the removal of the chiral auxiliary and applications of the released optically active building blocks in synthesis are featured.
1 Introduction
2 Types of Chiral Auxiliaries
2.1 Amides
2.2 Oxazolidines
2.3 Enecarbamates
2.4 Esters
2.5 Acetals
2.6 Enol Ethers
3 Removal of the Chiral Auxiliary
4 Chiral-Auxiliary-Mediated Epoxidations in Synthesis
5 Outlook
Key words
alkenes - mechanisms - oxidations - oxygen transfer - stereoselectivity - synthesis
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