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Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides.

Abstract:

Highly diastereoselective coupling reactions of enolates derived from butane-2,3-diacetal protected glycolic acids 1 and 2 and their alkylated derivatives with aldehydes are reported together with their efficient acid-catalysed deprotection to yield enantiopure anti-2,3-dihydroxyesters. A procedure to provide the corresponding syn-2,3-dihydroxyesters is also described in two cases, proceeding via an acylation-reduction sequence. An usual double addition reaction of butane-2,3-diacetal protect...

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Publisher copy:
10.1039/b412790k

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Organic and biomolecular chemistry More from this journal
Volume:
2
Issue:
24
Pages:
3618-3627
Publication date:
2004-12-01
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Language:
English
Keywords:
Pubs id:
pubs:52061
UUID:
uuid:fda3ecbc-11b0-41ed-bd29-12d6681d4b7e
Local pid:
pubs:52061
Source identifiers:
52061
Deposit date:
2012-12-20

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