title: 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 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.
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
authors.forename: Kevin
authors.initials: K
authors.lastname: Cheng
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Carroll
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
mesh_terms: D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry*
chemical_list: D004988:Ethers, Cyclic; D006847:Hydrocarbons, Iodinated; D017967:Zinc Compounds; C043657:cyclopropanol; C027946:methylene iodide