Face-selectivity in [4+2]-cycloadditions to novel polycyclic benzoquinones. Remarkable stereodirecting effects of a remote cyclopropane ring and an olefinic bond

Mehta, Goverdhan ; Droumaguet, Celine Le ; Islam, Kabirul ; Anoop, Anakuthil ; Jemmis, Eluvathingal D. (2003) Face-selectivity in [4+2]-cycloadditions to novel polycyclic benzoquinones. Remarkable stereodirecting effects of a remote cyclopropane ring and an olefinic bond Tetrahedron Letters, 44 (15). pp. 3109-3113. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4039(03)00504-5

Abstract

π-Face selectivity in Diels-Alder reactions between specially crafted bicyclo[2.2.2]octane-fused benzoquinones, where the dienophilic moiety is imbedded in an isosteric environment, can be modulated by a remote olefinic bond and a cyclopropane ring. Quantum mechanical calculations while reproducing the observed diastereoselectivities at the TS level indicate the involvement of ground state orbital effects.

Item Type:	Article
Source:	Copyright of this article belongs to Elsevier Science.
ID Code:	13677
Deposited On:	12 Nov 2010 15:32
Last Modified:	16 May 2016 22:48

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