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

Junfeng Yang, Alice Rérat, Yang Jie Lim, Corinne Gosmini, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

55 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2449-2453
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number9
DOIs
Publication statusPublished - 2017 Feb 20
Externally publishedYes

Keywords

  • C−H activation
  • asymmetric synthesis
  • cobalt
  • cyclizations
  • hydroacylation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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