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Molecular sieve controlled diastereoselectivity: effect in the palladium-catalyzed cyclization of cis-1,2-divinylcyclohexane with .alpha.-oxygen-substituted acids as chiral nucleophiles

Authors :
Peter Baeckstroem
Louise Tottie
Joergen Tegenfeldt
Christina Moberg
Andreas Heumann
Source :
The Journal of Organic Chemistry. 57:6579-6587
Publication Year :
1992
Publisher :
American Chemical Society (ACS), 1992.

Abstract

Molecular sieves have been shown to improve greatly the stereoselectivity in the palladium(II)-catalyzed reaction of cis-1,2-divinylcyclohene with chiral acids. Reactions run with molecular sieves and derivatives of (R)-lactic acids as nucleophiles always yielded products with S configuration at the newly formed chiral center in contrast to reactions without molecular sieves that gave products with either S or R configuration at this chiral center. It appears that this effect has not been observed previously

Details

ISSN :
15206904 and 00223263
Volume :
57
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi...........3051940c3822b1fa205d310ff3de36a2
Full Text :
https://doi.org/10.1021/jo00050a039