Experimental and Computational Studies for the Synthesis of Functionalized Cyclopropanes from 2‐Substituted Allylic Derivatives with Ethyl Diazoacetate

Author:

Zhao Chengtao1,Besset Tatiana1,Legault Claude Y.2ORCID,Jubault Philippe1ORCID

Affiliation:

1. INSA Rouen UNIROUEN CNRS COBRA (UMR 6014) Normandie Univ. 76000 Rouen France

2. Département de Chimie Université de Sherbrooke 2500 boul. de l'Université D1-3029 Sherbrooke Canada

Abstract

AbstractThe catalytic asymmetric synthesis of highly functionalized cyclopropanes from 2‐substituted allylic derivatives is reported. Using ethyl diazo acetate, the reaction, catalyzed by a chiral ruthenium complex (Ru(II)‐Pheox), furnished the corresponding easily separable cis and trans cyclopropanes in moderate to high yields (32‐97 %) and excellent ee (86‐99 %). This approach significantly extends the portfolio of accessible enantioenriched cyclopropanes from an underexplored class of olefins. DFT calculations suggest that an outer‐sphere mechanism is operative in this system.

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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