The tricyclo[2.1.0.02,5]pentan-3-one system: a new probe for the study of π-facial selectivity in nucleophilic additions

Mehta, Goverdhan ; Singh, S. Robindro ; Priyakumar, U. Deva ; Sastry, G. Narahari (2003) The tricyclo[2.1.0.02,5]pentan-3-one system: a new probe for the study of π-facial selectivity in nucleophilic additions Tetrahedron Letters, 44 (15). pp. 3101-3104. 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)00515-X

Abstract

Monosubstituted tricyclo[2.1.0.02,5]pentan-3-one derivatives have been synthesised and subjected to hydride reduction. Quite unexpectedly and in contrast to earlier observations in related systems, anti-selectivity has been encountered in these substrates. Computational studies employing various models reproduce the observed facial preference and indicate that the causative factor for the anti-preference could be the polarization of the C1-C5 strained σ bond.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
ID Code:29003
Deposited On:18 Dec 2010 05:43
Last Modified:17 May 2016 11:59

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