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Asymmetric synthesis of (R)-hexane-1,5-diol and (R)-hex-3-ene-1,5-diol via a tandem asymmetric conjugate addition stereospecific Meisenheimer rearrangement protocol

Abstract:
Stereoselective conjugate addition of (R)-lithium N,α-dimethylbenzylamide to tert-butyl (E,E)-hexa-2,4-dienoate, followed by reduction of the ester to the corresponding alcohol, affords a substrate which undergoes, on oxidation, a stereospecific Meisenheimer rearrangement to give a single diastereomer of the corresponding trialkylhydroxylamine. Cleavage of the N-O bond gives (R)-hex-3-ene-1,5-diol and subsequent hydrogenation of the double bond affords (R)-hexane-1,5-diol in high e.e.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON-ASYMMETRY
Volume:
7
Issue:
4
Pages:
1001-1004
Publication date:
1996-04-05
DOI:
ISSN:
0957-4166
URN:
uuid:6fb51fdc-f74b-4868-b4c3-6f23cd2e9bd8
Source identifiers:
110845
Local pid:
pubs:110845
Language:
English

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