Amino-Catalyzed Reactions of Aldehydes with Chiral Nitroalkenes.

Org Lett

Organic Chemistry, Facultat de Química, Universitat de Barcelona, Diagonal 645, 08028 Barcelona, Catalonia, Spain.

Published: February 2021

Chiral nitroalkenes are used for the first time in Michael additions of aldehydes, catalyzed by pyrrolidine derivatives. They yield the same major stereoisomer with either ()-proline or ()-proline, but this asymmetric induction does not overcome the effect of sterically more congested catalysts. Nitrocyclobutane intermediates are often formed, which are more stable than those from ()-1-nitro-2-phenylethene. The cyclobutanes and final products were characterized by 2D NMR and chemical correlations.

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http://dx.doi.org/10.1021/acs.orglett.0c03609DOI Listing

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