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Highly stereoselective oxy-michael additions to beta,gamma-unsaturated alpha-keto esters: rapid enantioselective synthesis of 3-hydroxybutenolides.

Abstract:
The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl delta-lactol to gamma-substituted beta,gamma-unsaturated alpha-keto esters leading to the direct formation of THP*-protected gamma-hydroxy alpha-keto ester derivatives is described. Subsequent acid-mediated deprotection affords the 3-hydroxybutenolides in high yields.
Publication status:
Published

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Publisher copy:
10.1021/ol702693m

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic letters
Volume:
10
Issue:
4
Pages:
565-567
Publication date:
2008-02-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:1fb45910-9f58-408a-9383-9b35fe60627f
Source identifiers:
34105
Local pid:
pubs:34105
Language:
English

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