Chiral-Auxiliary-Controlled Diastereoselective Epoxidations

Waldemar Adam; Aimin Zhang

doi:10.1055/s-2005-865214

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Synlett 2005(7): 1047-1072
DOI: 10.1055/s-2005-865214

ACCOUNT

Chiral-Auxiliary-Controlled Diastereoselective Epoxidations

Waldemar Adam^a,b, Aimin Zhang*^c
^a Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany
^b Department of Chemistry, Facundo Bueso 110, University of Puerto Rico, Rio Piedras, Puerto Rico 00931, USA
e-Mail: wadam@chemie.uni-wuerzburg.de; e-Mail: wadam@adam.uprr.pr;
^c Department of Chemistry, NSC 815, New York State University at Buffalo, Buffalo, NY, 14260, USA
e-Mail: azhang2@buffalo.edu;

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Publication History

Received 13 December 2004
Publication Date:
14 April 2005 (online)

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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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