4.8 Article

Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 46, Pages 13711-13714

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506701

Keywords

asymmetric catalysis; heterocycles; nucleophilic addition; organocatalysis; synthetic methods

Funding

  1. HKUST, Hong Kong RGC [GRF 604513, ECS605812, M-HKUST607/12]

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Described herein is a general and mild catalytic asymmetric 1,6-conjugate addition of para-quinone methides (p-QMs), a class of challenging reactions with previous limited success. Benefiting from chiral BrOnsted acid catalysis, which allows insitu formation of p-QMs, our reaction expands the scope to general p-QMs with various substitution patterns. It also enables efficient intermolecular formation of all-carbon quaternary stereocenters with high enantioselectivity.

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