research article
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
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.
Type
research article
Author(s)
Jones, G. R.
Date Issued
1993
Issue
9
Start page
769
End page
771
Subjects
Editorial or Peer reviewed
REVIEWED
Written at
EPFL
EPFL units
Available on Infoscience
November 9, 2005
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