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Asymmetric synthesis of (R)-hexane-1,5-diol, (R)-hex-3-ene-1,5-diol and (R)-6-methylhept-5-en-2-ol (sulcatol) employing a tandem asymmetric conjugate addition and stereospecific Meisenheimer rearrangement protocol

Abstract:

Highly stereoselective conjugate addition of lithium (R)-N-methyl-(α-methylbenzyl)amide to tert-butyl (E,E)-hexa-2,4-dienoate, followed by reduction of the ester to the corresponding alcohol, affords a substrate which undergoes, upon oxidation, a stereospecific Meisenheimer rearrangement to give a single diastereomer of the corresponding trialkylhydroxylamine. The analogous N-benzyl adduct gives lower yields in the oxidation-rearrangement reaction. If the ester is not reduced to the alcohol, ...

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Publication status:
Published

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Publisher copy:
10.1039/p19960002467

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
20
Pages:
2467-2477
Publication date:
1996-10-21
DOI:
EISSN:
1364-5463
ISSN:
1472-7781
URN:
uuid:f1b74429-5fa3-42c7-84a1-0394b276c298
Source identifiers:
110839
Local pid:
pubs:110839

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