Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Vol. 80 Commemorative Accounts
Chiral Glycolate Equivalents for the Asymmetric Synthesis of α-Hydroxycarbonyl Compounds
Steven V. LeyTom D. SheppardRebecca M. MyersMukund S. Chorghade
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JOURNAL FREE ACCESS

2007 Volume 80 Issue 8 Pages 1451-1472

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Abstract

Chiral glycolic acid equivalents are used extensively for the enantioselective synthesis of α-hydroxycarbonyl compounds. Their efficacy in enolate reactions and their utility in synthetic applications are discussed, highlighting the relevance of these methods to natural product synthesis.

Hydroxycarbonyl compounds are valuable intermediates in asymmetric synthesis, particularly in the preparation of complex structures such as terpenes, carbohydrates, and alkaloids. In addition, the use of chiral glycolic acid equivalents has been the approach of choice for α-hydroxycarbonyl-containing natural products such as herbarumin II and rapamycin. Fullsize Image
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© 2007 The Chemical Society of Japan
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