Literature DB >> 21462964

Diasteroselective preparation of cyclopropanols using methylene bis(iodozinc).

Kevin Cheng1, Patrick J Carroll, Patrick J Walsh.   

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.

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Year:  2011        PMID： 21462964      PMCID： PMC3084887          DOI： 10.1021/ol200597h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  25 in total

Review 1.  Biosynthesis and metabolism of cyclopropane rings in natural compounds.

Authors:  Ludger A Wessjohann; Wolfgang Brandt; Thies Thiemann
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  Cross-Coupling Reactions between alpha,beta-Unsaturated Ketones and Aldehydes with CrCl(2): Aldol Condensation and Cyclopropanol Formation Financial support by a Grant-in-Aid for Scientific Research on Priority Area No. 706 from the Ministry of Education, Science, Sports and Culture of Japan is gratefully acknowledged. We would also like to thank Professor Ilhyong Ryu of Osaka Prefecture University for helpful discussions, and Dr. Teruhiko Ishikawa of Okayama University for conducting the NOE experiments.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-08-04       Impact factor: 15.336

3.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

4.  Diastereoselective zinco-cyclopropanation of chiral allylic alcohols with gem-dizinc carbenoids.

Authors:  Jean-François Fournier; Simon Mathieu; André B Charette
Journal:  J Am Chem Soc       Date:  2005-09-28       Impact factor: 15.419

5.  Reaction pathway of methylenation of carbonyl compounds with bis(iodozincio)methane.

Authors:  Mutsumi Sada; Shinsuke Komagawa; Masanobu Uchiyama; Masami Kobata; Tsuyoshi Mizuno; Kiitiro Utimoto; Koichiro Oshima; Seijiro Matsubara
Journal:  J Am Chem Soc       Date:  2010-11-17       Impact factor: 15.419

6.  Catalytic enantioselective hydroboration of cyclopropenes.

Authors:  Marina Rubina; Michael Rubin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2003-06-18       Impact factor: 15.419

7.  Applications of 1-alkenyl-1,1-heterobimetallics in the stereoselective synthesis of cyclopropylboronate esters, trisubstituted cyclopropanols and 2,3-disubstituted cyclobutanones.

Authors:  Mahmud M Hussain; Hongmei Li; Nusrah Hussain; Mercedes Ureña; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2009-05-13       Impact factor: 15.419

8.  Stereospecific construction of chiral tertiary and quaternary carbon by nucleophilic cyclopropanation with bis(iodozincio)methane.

Authors:  Kenichi Nomura; Seijiro Matsubara
Journal:  Chem Asian J       Date:  2010-01-04

9.  Nucleophilic cyclopropanation reaction with bis(iodozincio)methane by 1,4-addition to alpha,beta-unsaturated carbonyl compounds.

Authors:  Kenichi Nomura; Takaharu Hirayama; Seijiro Matsubara
Journal:  Chem Asian J       Date:  2009-08-03

10.  Enantioselective synthesis of 1,2,3-trisubstituted cyclopropanes using gem-dizinc reagents.

Authors:  Lucie E Zimmer; André B Charette
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419
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  2 in total

Review 1.  Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development.

Authors:  Jennifer K Matsui; Simon B Lang; Drew R Heitz; Gary A Molander
Journal:  ACS Catal       Date:  2017-03-14       Impact factor: 13.084

2.  Diastereo- and enantioselective preparation of cyclopropanol derivatives.

Authors:  Marwan Simaan; Ilan Marek
Journal:  Beilstein J Org Chem       Date:  2019-03-21       Impact factor: 2.883
  2 in total

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