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The allylic nucleophilic substitution of Morita-Baylis-Hillman acetates with isocyanides: a facile synthesis of trisubstituted olefins
Authors:J.S. Yadav  B.V. Subba Reddy  Ashutosh Pratap Singh  Nilanjan Majumder
Affiliation:Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
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.
Keywords:Morita-Baylis-Hillman acetates   SN2&prime   substitution   TosMIC   Alkylation
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