Chirality transfer in palladium catalyzed reactions of allylammonium salts

Takayuki Doi, Arata Yanagisawa, Masahiro Miyazawa, Keiji Yamamoto

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst. The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration due probably to a prior isomerization from anti to syn-π-allylpalladium intermediate (14→15). The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.

Original languageEnglish
Pages (from-to)389-392
Number of pages4
JournalTetrahedron: Asymmetry
Volume6
Issue number2
DOIs
Publication statusPublished - 1995 Feb
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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