Catalytic Asymmetric Cyclopropanation of 1,1-Disubstituted Electron-Deficient Alkenes with Dimethyl Diazomalonate

Abstract The catalytic asymmetric synthesis of enantioenriched 1,1-cyclopropane diesters is reported. A reaction combining Rh2(R-p-BTPCP)4 as the chiral catalyst, dimethyl diazomalonate, and 1,1-disubstituted electron-poor alkenes was developed, providing access to a broad range of tetrasubstituted enantioenriched cyclopropanes. The reaction proceeded smoothly, and the products were isolated in moderate to good yields with good to excellent enantioselectivities.

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Publication Details

Journal
Organic Letters
Published
2026-10-07
DOI
https://doi.org/10.1021/acs.orglett.6c03955
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
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article

Catalytic Asymmetric Cyclopropanation of 1,1-Disubstituted Electron-Deficient Alkenes with Dimethyl Diazomalonate

Thomas Poisson, André B. Charette, Charlotte Noël, Philippe Jubault
Organic Letters
Cyclopropane Reaction Mechanisms
article

Catalytic Asymmetric Cyclopropanation of 1,1-Disubstituted Electron-Deficient Alkenes with Dimethyl Diazomalonate

Thomas Poisson, André B. Charette, Charlotte Noël, Philippe Jubault
article en

Abstract

Abstract The catalytic asymmetric synthesis of enantioenriched 1,1-cyclopropane diesters is reported. A reaction combining Rh2(R-p-BTPCP)4 as the chiral catalyst, dimethyl diazomalonate, and 1,1-disubstituted electron-poor alkenes was developed, providing access to a broad range of tetrasubstituted enantioenriched cyclopropanes. The reaction proceeded smoothly, and the products were isolated in moderate to good yields with good to excellent enantioselectivities.

Organic Letters
Normandie Université (FR), Université de Rouen Normandie (FR), Institut National des Sciences Appliquées Rouen Normandie (FR)
Openalex Percentile: Top 24%
Cyclopropane Reaction Mechanisms
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