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Synthesis 2014; 46(17): 2272-2282
DOI: 10.1055/s-0034-1378514
DOI: 10.1055/s-0034-1378514
feature article
Preparation of the Zinc Enolate Equivalent of Amides by Zinciomethylation of Isocyanates: Catalytic Asymmetric Reformatsky-Type Reaction
Further Information
Publication History
Received: 02 June 2014
Accepted after revision: 25 June 2014
Publication Date:
31 July 2014 (online)
Abstract
Bis(iodozincio)methane [CH2(ZnI)2] transforms isocyanates (R–N=C=O) into the enolate equivalent of amides via zinciomethylation. The reactivity of the enolate equivalent as a nucleophile toward aldehydes depends on the R group of the isocyanate. For the enolate equivalent formed from phenyl isocyanate, the addition of a catalytic amount of an optically active amino alcohol, which acts as an activator, leads to a catalytic asymmetric Reformatsky-type reaction.
Key words
organozinc reagents - dizinc compounds - Reformatsky reaction - asymmetric synthesis - catalysisSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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