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.


Published in:
Journal of the Chemical Society, Chemical Communications, 9, 769-771
Year:
1993
ISSN:
0022-4936
Keywords:
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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