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ASYMMETRIC-SYNTHESIS OF BETA-AMINO-ALPHA-HYDROXY ACIDS VIA DIASTEREOSELECTIVE HYDROXYLATION OF HOMOCHIRAL BETA-AMINO ENOLATES

Abstract:

The highly diastereoselective conjugate addition of lithium N-benzyl-N-α-methylbenzylamide with enoate acceptors, and the electrophilic hydroxylation of the resultant β-amino enolates with (camphorsulfonyl)oxaziridine, is identified as a direct and general strategy for the asymmetric synthesis of homochiral β-amino-α-hydroxy acids and their derivatives. A structurally diverse array of β-amino enolate substrates can be hydroxylated with generally excellent anti diastereoselectivity (>90% d....

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Publication status:
Published

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Publisher copy:
10.1039/p19940002373

Authors


BUNNAGE, M More by this author
CHERNEGA, A More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
GOODWIN, C More by this author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
17
Pages:
2373-2384
Publication date:
1994-09-07
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
URN:
uuid:8871a71a-4615-4587-a87f-ae2555b0b330
Source identifiers:
110862
Local pid:
pubs:110862

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