Improved protocol for the diastereoselective cyclopropanation of alkenes using geminal dizinc carbenoids: A study on the effect of zinc iodide

European Journal of Organic Chemistry

Volumn , Issue 7, 2004, Pages 1401-1404

  Fournier, Jean François ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Alkenes; Carbenoids; Carbocycles; Cycloaddition; Zinc

Indexed keywords

ALKENE DERIVATIVE; CARBENOID; IODINE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CYCLOPROPANATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 4544338161     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400029     Document Type: Article

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22. The relative stereochemistry for the electrophile insertion is that shown in Schemes 2 and 3; it was established by deuteration of the cyclopropylzinc reagent, which led to 7b and 9b exclusively.
23. Detailed kinetic studies were inconclusive because of the heterogeneous nature of the reaction mixture, and the difficulty in controlling the exact initial concentration of 2c (carbenoids of type 2 undergo decomposition and are subject to various equilibria).