4.8 Article

Rationally Designed Multifunctional Supramolecular Iminium Catalysis: Direct Vinylogous Michael Addition of Unmodified Linear Dienol Substrates

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 51, Pages 14128-14131

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406786

Keywords

asymmetric catalysis; Michael addition; regioselectivity; supramolecular chemistry; synthetic methods

Funding

  1. NSFC [21372105, 21302075, 21032005, 21172097]
  2. International S&T Cooperation Program of China [2013DFR70580]
  3. 111 program from MOE of P.R. China

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The development of a direct vinylogous Michael addition of linear nucleophilic substrates is a long-standing challenge because of the poor reactivity and the considerable difficulty in controlling regioselectivity. By employing a rationally designed multifunctional supramolecular iminium catalysis strategy, the first direct vinylogous Michael addition of unmodified linear substrates to alpha,beta-unsaturated aldehydes, to afford chiral 1,7-dioxo compounds with good yields and excellent regio- as well as enantioselectivity, has been developed.

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