Mechanism of remote conjugate addition of a lithium organocuprate to a polyconjugated carbonyl compound

Naohiko Yoshikai, Tatsuya Yamashita, Eiichi Nakamura

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Passing the buck: Rapid copper migration along the conjugated system results in regioselective remote conjugate addition of a lithium organocuprate to a polyenynyl carbonyl compound, as revealed by density-functional calculations (see scheme). The unique structural/electronic properties of the σ/π-allenyl-copper(III) intermediates are responsible for the selective C-C bond formation at the terminal acetylenic position. (Chemical Equation Presented)

Original languageEnglish
Pages (from-to)4721-4723
Number of pages3
JournalAngewandte Chemie - International Edition
Volume44
Issue number30
DOIs
Publication statusPublished - 2005 Jul 25
Externally publishedYes

Keywords

  • Conjugate addition
  • Density functional calculations
  • Organocuprates
  • Reaction mechanisms
  • Regioselectivity

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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