Cyclopropene Derivatives as Precursors to Enantioenriched Cyclopropanols and n-Butenals Possessing Quaternary Carbon Stereocenters - INRAE - Institut national de recherche pour l’agriculture, l’alimentation et l’environnement Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie International Edition Année : 2015

Cyclopropene Derivatives as Precursors to Enantioenriched Cyclopropanols and n-Butenals Possessing Quaternary Carbon Stereocenters

Résumé

The diastereoselective carbocupration reaction of cyclopropenylmethyl ethers followed by addition of oxenoid leads to the formation of diastereo- and enantiomerically enriched 2,2,3,3-tetrasubstituted cyclopropanol derivatives. Ring fragmentation of the copper cyclopropanolate leads to acyclic butenal derivatives possessing enantiomerically enriched a-quaternary carbon stereocenters in a single-pot operation.

Dates et versions

hal-02631404 , version 1 (27-05-2020)

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Citer

Marwan Simaan, Pierre-Olivier Delaye, Min Shi, Ilan Marek. Cyclopropene Derivatives as Precursors to Enantioenriched Cyclopropanols and n-Butenals Possessing Quaternary Carbon Stereocenters. Angewandte Chemie International Edition, 2015, 54 (42), pp.12345 - 12348. ⟨10.1002/anie.201412440⟩. ⟨hal-02631404⟩
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