4.8 Article

Cobalt-Catalyzed Enantio- and Diastereoselective Intramolecular Hydroacylation of Trisubstituted Alkenes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 9, Pages 2449-2453

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611518

Keywords

asymmetric synthesis; C-H activation; cobalt; cyclizations; hydroacylation

Funding

  1. Singapore Ministry of Education [RG 5/14]
  2. Nanyang Technological University
  3. JST, CREST

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Enantio- and diastereoselective synthesis of trans-2,3-disubstituted indanones is achieved by intramolecular hydroacylation of 2-alkenylbenzaldehydes bearing trisubstituted alkenyl groups under cobalt-chiral diphosphine catalysis. Notably, a high level of enantioselectivity is induced regardless of the stereochemistry (E/Z ratio) of the alkenyl group of the starting material. Deuterium-labeling experiments shed light on the productive reaction pathways of the E- and Z-isomers.

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