π-Face selectivities in nucleophilic additions to 2-endo-arylnorbornan-7-ones: the role of through-space electrostatic interactions

Mehta, Goverdhan ; Khan, Faiz Ahmed ; Mohal, Narinder ; Narayan Namboothiri, I. N. ; Kalyanaraman, P. ; Chandrasekhar, Jayaraman (1996) π-Face selectivities in nucleophilic additions to 2-endo-arylnorbornan-7-ones: the role of through-space electrostatic interactions Journal of the Chemical Society, Perkin Transactions 1 (22). pp. 2665-2667. ISSN 0300-922X

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1996...

Related URL: http://dx.doi.org/10.1039/P19960002665

Abstract

Experimental diastereoselectivities in hydride reduction of 2-endo-arylnorbornan-7-ones and computed transition state energetics reveal that the facial selectivity in these systems is predominantly determined by repulsions between the approaching nucleophile and the electron cloud of the aryl ring.

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