Pi-Facial Diastereoselectivity in the Electrophilic and Electrophilic Nucleophilic Additions to Dimethyl (1r,2r,3s,4s)-Bicyclo[2.2.2]Oct-5-Ene-2,3-Dicarboxylate
1993
Abstract
The pi-facial selectivity of attack of electrophilic species (OsO4, m-ClC6H4CO3H, BH3) on the sterically unbiased dimethyl (1R,2R,3S,4S)-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylate is controlled syn to the exo electron-withdrawing ester substituents, and the reactions of phenylselenyl chloride and phenylsulfenyl chloride show opposing diastereoselectivities, which can be explained using the Cieplak transition state theory.
Details
Title
Pi-Facial Diastereoselectivity in the Electrophilic and Electrophilic Nucleophilic Additions to Dimethyl (1r,2r,3s,4s)-Bicyclo[2.2.2]Oct-5-Ene-2,3-Dicarboxylate
Author(s)
Jones, G. R. ; Vogel, P.
Published in
Journal of the Chemical Society, Chemical Communications
Issue
9
Pages
769-771
Date
1993
ISSN
0022-4936
Keywords
Laboratories
LGSA
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > SB Archives > LGSA - Laboratory of Glycochemistry and Asymmetric Synthesis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date
2005-11-09