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

Mehta, Goverdhan and Droumaguet, Celine Le and Islam, Kabirul and Anoop, Anakuthil and 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. In: Tetrahedron Letters, 44 (15). pp. 3109-3113.

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Abstract

Pi-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:	Journal Article
Publication:	Tetrahedron Letters
Publisher:	Elsevier Science
Additional Information:	Copyright for this article belongs to Elsevier Science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	26 Jul 2004
Last Modified:	19 Sep 2010 04:14
URI:	http://eprints.iisc.ac.in/id/eprint/1182

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