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Synthesis 2013; 45(13): 1807-1814
DOI: 10.1055/s-0033-1338876
DOI: 10.1055/s-0033-1338876
paper
Diastereoselective Syntheses of Highly Substituted Methylenecyclopropanes via Copper- or Iron-Catalyzed Reactions of 1,2-Disubstituted 3-(Hydroxymethyl)cyclopropenes with Grignard Reagents
Further Information
Publication History
Received: 08 April 2013
Accepted after revision: 08 May 2013
Publication Date:
06 June 2013 (online)
Dedicated to Scott Denmark in recognition of his contributions to the chemistry of strained molecules
Abstract
Described are diastereoselective syntheses of highly substituted methylenecyclopropanes from 1,2-disubstituted 3-(hydroxymethyl)cyclopropenes with allylic ether leaving groups, compounds that were constructed via alkylation of cyclopropenecarboxylic acid dianions. Substitution reactions of 1,2-disubstituted 3-(hydroxymethyl)cyclopropenes with Grignard reagents proceed with good yield and high diastereoselectivity. Under copper(I)-catalyzed conditions, the substitution reactions proceed to give syn-addition products, whereas Fe(acac)3 catalysis gives the products of anti-addition.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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