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Alkylation and aldol reactions of acyl derivatives of N-1-(1 '-naphthyl)ethyl-O-tert-butylhydroxylamine: asymmetric synthesis of alpha-alkoxy-, alpha-substituted-beta-alkoxy- and alpha,beta-dialkoxyaldehydes

Abstract:

Treatment of a range of O-protected glycolate derivatives of the chiral auxiliary N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine with KHMDS in the presence of 18-crown-6 followed by addition of an alkyl halide generates α-substituted derivatives with very high levels of diastereoselectivity. Alternatively, reaction of the potassium enolate of a propanoate or O-protected glycolate derivative of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine with a range of aldehydes gives syn-aldol product...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2010.03.105

Authors


Chernega, AN More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Fletcher, AM More by this author
Goodwin, CJ More by this author
Hepworth, D More by this author
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Journal:
TETRAHEDRON
Volume:
66
Issue:
23
Pages:
4167-4194
Publication date:
2010-06-05
DOI:
ISSN:
0040-4020
URN:
uuid:df7130bb-fa2a-414c-9d79-d0617367e768
Source identifiers:
110645
Local pid:
pubs:110645

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