SYNTHESIS AND ANIONICALLY INDUCED DOMINO REACTIONS OF CHIRAL ALPHA-BROMO ALPHA,BETA-UNSATURATED ESTERS

Authors
BRAUN NA BURKLE U FETH MP KLEIN I SPITZNER D
Citation
Na. Braun et al., SYNTHESIS AND ANIONICALLY INDUCED DOMINO REACTIONS OF CHIRAL ALPHA-BROMO ALPHA,BETA-UNSATURATED ESTERS, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (8), 1998, pp. 1569-1576
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY → ACNP
ISSN journal
1434193X
Issue
8
Year of publication
1998
Pages
1569 - 1576
Database
ISI
SICI code
1434-193X(1998):8<1569:SAAIDR>2.0.ZU;2-Z
Abstract
The chiral alpha-bromo alpha,beta-unsaturated esters 3 and 9 are prepa red by asymmetric Sharpless dihydroxylation (AD) of 5 and from ester 7 and the chiral diols 8 by transacetalization, respectively. Both type s of alpha-bromo alpha,beta-unsaturated ester react with the kinetic L ithium dienolates of enone 10 to give functionalized tricyclo[3.2.1.0( 2,7)]octanes 11. Esters 3 give one single diastereomer (de greater tha n or equal to 95%), whereas mixtures of diastereomers (de 28 to 46%) a re obtained with the esters 9.