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Conjugate addition of organocopper reagents to gamma-alkoxybutenolides and application to the synthesis of non-racemic alkyl cyclopentenones.

Abstract:
Simple organocopper reagents are shown to undergo anti-stereoselective 1,4-addition to menthyloxy-substituted lactone 1 in the presence of BF3.OEt2; the Lewis acid causes partial epimerisation of the acetal centre after conjugate addition. Enolate alkylation of the adducts leads to di- and trisubstituted lactones that are converted, in favourable cases, into di- and trisubstituted cyclopentenones.
Publication status:
Published

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Publisher copy:
10.1039/b408255a

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Organic and biomolecular chemistry
Volume:
2
Issue:
20
Pages:
2988-2997
Publication date:
2004-10-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:469f7b15-b499-42ed-9949-e1898aab5075
Source identifiers:
55231
Local pid:
pubs:55231

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