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Diasteroselective preparation of cyclopropanols using methylene bis(iodozinc).

ABSTRACT: A diastereoselective synthesis of trans-2-substituted cyclopropanols is outlined. Bimetallic CH(2)(ZnI)(2) was found to react with ?-chloroaldehydes to give cyclopropanols in yields of 64-89% and dr's ? 10:1. The high trans-selectivity resulted from equilibration of the cyclopropoxide intermediates.

SUBMITTER: Cheng K

PROVIDER: S-EPMC3084887 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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Diasteroselective preparation of cyclopropanols using methylene bis(iodozinc).

Cheng Kevin K Carroll Patrick J PJ Walsh Patrick J PJ

Organic letters 20110404 9

A diastereoselective synthesis of trans-2-substituted cyclopropanols is outlined. Bimetallic CH(2)(ZnI)(2) was found to react with α-chloroaldehydes to give cyclopropanols in yields of 64-89% and dr's ≥ 10:1. The high trans-selectivity resulted from equilibration of the cyclopropoxide intermediates. ...[more]

PMID: 21462964

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