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The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: a chiral Weinreb amide equivalent.

Abstract:

The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine is readily prepared from N-hydroxyphthalimide in four steps, with resolution giving access to both enantiomers in > 98% ee, on a multigram (> 25 g) scale. Conversion to a range of N-acyl derivatives, followed by highly diastereoselective alkylation (> or = 94% de) gives the corresponding chiral, 2-substituted derivatives as single diastereoisomers (> 98% de) after chromatography. Reductive cleavage with LiAlH(4)...

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Publication status:
Published

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Publisher copy:
10.1021/ol901174t

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Journal:
Organic letters
Volume:
11
Issue:
15
Pages:
3254-3257
Publication date:
2009-08-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:dcd49f02-6731-4167-83e2-0a8f91cc30bb
Source identifiers:
110649
Local pid:
pubs:110649

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