Catalytic asymmetric allylic transfer reactions for the enantioselective synthesis of dienyl and enynyl alcohols

Citation
Cm. Yu et al., Catalytic asymmetric allylic transfer reactions for the enantioselective synthesis of dienyl and enynyl alcohols, EUR J ORG C, (6), 2001, pp. 1143-1148
Citations number
35
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
6
Year of publication
2001
Pages
1143 - 1148
Database
ISI
SICI code
1434-193X(200103):6<1143:CAATRF>2.0.ZU;2-P
Abstract
Efficient catalytic asymmetric allylic transfer reactions of achiral aldehy des with 2-ethynyl- and 2-ethenyl-2-propenyl-stannane promoted by BINOL-Ti- IV complex with synergetic reagent are achieved for the synthesis of homoen ynyl- and dienyl alcohols with high levels of enantioselectivity. The range of enantioselectivity is 84-99% ee with good chemical yields. The applicat ion of catalytic asymmetric dienylation in a single operation was exemplifi ed by the enantioselective synthesis of naturally occurring (-)-Ipsdienol a nd (-)-Ipsenol.