4.8 Article

Direct Asymmetric Vinylogous and Bisvinylogous Mannich-Type Reaction Catalyzed by a Copper(I) Complex

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 6, Pages 2196-2199

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b13042

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Funding

  1. Thousand Youth Talents Plan
  2. National Natural Sciences Foundation of China [21672235]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  4. Shanghai Rising-Star Plan [15QA1404600]
  5. CAS Key Laboratory of Synthetic Chemistry of Natural Substances and Shanghai Institute of Organic Chemistry

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A direct catalytic asymmetric vinylogous Mannich-type reaction has been disclosed in good yield, excellent regio-, diastereo- and enantioselectivity. The key to control the regioselectivity is the combination of a bulky N-acylpyrazole and a bulky bisphosphine ligand. The catalytic system was extended to a bisvinylogous Mannich-type reaction by changing the ligand. The synthetic utility of the vinylogous products was demonstrated by several transformations.

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