The allylic nucleophilic substitution of Morita-Baylis-Hillman acetates with isocyanides: a facile synthesis of trisubstituted olefins

Yadav, J. S. ; Subba Reddy, B. V. ; Pratap Singh, Ashutosh ; Majumder, Nilanjan (2010) The allylic nucleophilic substitution of Morita-Baylis-Hillman acetates with isocyanides: a facile synthesis of trisubstituted olefins Tetrahedron Letters, 51 (17). pp. 2291-2294. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2010.02.130

Abstract

Morita-Baylis-Hillman acetates undergo smooth allylic nucleophilic substitution (SN2') with tosylmethyl isocyanide (TosMIC) in the presence of a catalytic amount of BF3·OEt2 under mild conditions to furnish trisubstituted olefins in high yields with (E)-stereoselectivity.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Morita-Baylis-Hillman Acetates; SN2' Substitution; TosMIC; Alkylation
ID Code:58864
Deposited On:02 Sep 2011 03:40
Last Modified:02 Sep 2011 03:40

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