Syntheses via vinyl sulfones, part 85. Syntheses of highly substituted enantiopure C6 and C7 enones

Enantiopure epoxyvinyl sulfones SS-9a, SS-9b, produced from Jacobsen epoxidation of 2-phenylsulfonyl 1,3-cyclohexa- and cycloheptadiene, are used as a template for the construction of substituted cycloalkenones and as chiral synthetic equivalents of enones a and b. The addition of carbon nucleophile...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 124; no. 37; pp. 11093 - 11101
Main Authors Evarts, J, Torres, E, Fuchs, PL
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 18.09.2002
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALPHA,BETA-UNSATURATED KETONES
CHIRAL CYCLOHEXADIENONE
VERSATILE
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Summary:Enantiopure epoxyvinyl sulfones SS-9a, SS-9b, produced from Jacobsen epoxidation of 2-phenylsulfonyl 1,3-cyclohexa- and cycloheptadiene, are used as a template for the construction of substituted cycloalkenones and as chiral synthetic equivalents of enones a and b. The addition of carbon nucleophiles to SS-9a, SS-9b is high yielding and stereospecific. Enantiopure alpha,beta- and gamma-substituted cycloalkenones are easily constructed using a variety of methods.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja026760m