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Highly stereoselective oxy-Michael additions to alpha,beta-disubstituted nitro olefins: asymmetric synthesis of pseudo-norephedrine derivatives and THP* protected alpha-hydroxy ketones.

Abstract:

The "naked" anion of (S)-6-methyl delta lactol undergoes efficient oxy-Michael addition to alpha,beta-disubstituted nitro olefins to give the THP* protected Henry products with excellent (95-->98% de) stereocontrol at the beta-position and moderate (up to 3 : 1) stereocontrol at the alpha-position in favour of the syn-diastereoisomer. Nitro group reduction with in situN-Boc protection and THP* removal provides alpha,beta-disubstituted ethanolamine derivatives, while treatment with tetrapro...

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Publication status:
Published

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Publisher copy:
10.1039/b406804c

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic and biomolecular chemistry
Volume:
2
Issue:
20
Pages:
2932-2934
Publication date:
2004-10-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:712232d5-d618-4ed1-b1ec-7ce39d2774e7
Source identifiers:
52059
Local pid:
pubs:52059

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