The X-ray structure of 4a and MNDO optimized geometries of related 7-norbornenone derivatives show a clear tilt of the carbonyl bridge away from the CC double bond. The preferred reduction from the more hindered face of the diester reveals the electron/electrostatic origin of π - facial selectivity in these systems. © 1992.

Faiz Ahmed Khan

Department of Chemistry

V.A. Kumar

K. Venkatesan

B. Ganguly

J. Chandrasekhar

G. Mehta

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Tetrahedron Letters

Ground state geometric distortions Vs distal substituent effects in determining the β-facial selectivity in 7-norbornenones

Journal	Tetrahedron Letters
ISSN	00404039