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Angew Chem Int Ed Engl. 2017 Aug 1;56(32):9487-9491. doi: 10.1002/anie.201705546. Epub 2017 Jul 10.

Catalyst-Controlled, Enantioselective, and Diastereodivergent Conjugate Addition of Aldehydes to Electron-Deficient Olefins.

Author information

1
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan.
2
Department of Chemistry, Aichi University of Education, Igaya-cho, Kariya, Aichi, 448-8542, Japan.

Abstract

A chiral-amine-catalyzed enantioselective and diastereodivergent method for aldehyde addition to electron-deficient olefins is presented. Hydrogen bonding was used as a control element to achieve unusual anti selectivity, which was further elucidated through mechanistic and computational studies.

KEYWORDS:

Michael addition; aldehydes; asymmetric catalysis; organocatalysis; stereodivergence

PMID:
28632909
DOI:
10.1002/anie.201705546

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