Alternate mode of palladium-catalyzed alkynyliminium ion cyclizations affording stereodefined N-alkyl-3-alkylidenepyrrolidines

Hirokazu Tsukamoto, Mitsugu Shiraishi, Takayuki Doi

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Pd/P(c-C6H11)3-catalyzed alkynyliminium ion cyclization in the presence of organoboronic acids affords stereodefined N-alkyl-3-alkylidenepyrrolidines. The distinctive cis-selective addition of the boronic acids and the iminium ions across the alkyne would result from favored 5-exo- or 6-exo-dig cyclization through oxidative addition of the formaldiminium ions to Pd(0).

Original languageEnglish
Pages (from-to)5932-5935
Number of pages4
JournalOrganic letters
Volume15
Issue number23
DOIs
Publication statusPublished - 2013 Dec 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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