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Highly diastereoselective oxy-Michael additions of enantiopure delta-lactol anions to nitroalkenes: asymmetric synthesis of 1,2-amino alcohols.

Abstract:
The "naked" alkoxide 1 of (S)-6-methyl-δ-lactol acts as an excellent chiral hydroxide equivalent in highly diastereoselective oxy-Michael additions to nitroalkenes (see scheme). The excellent stereoinduction arises from what becomes a superb protecting group in the resulting 1,2-amino alcohol products. R1 = alkyl, aryl, furanyl, thiophenyl; R2,R 3 = -(CH2)3CHCH3O-.
Publication status:
Published

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Publisher copy:
10.1002/anie.200352007

Authors


Adderley, NJ More by this author
Buchanan, DJ More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Lainé, DI More by this author
Journal:
Angewandte Chemie (International ed. in English)
Volume:
42
Issue:
35
Pages:
4241-4244
Publication date:
2003-09-05
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
URN:
uuid:4b648aa1-9c38-48d4-a006-975b66457e00
Source identifiers:
52056
Local pid:
pubs:52056

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