Catalytic asymmetric desymmetrization of meso-diamide derivatives through enantioselective N-allylation with a chiral π-allyl Pd catalyst

Improvement and reversal of the enantioselectivity

Osamu Kitagawa, Shinichi Matsuo, Kanako Yotsumoto, Takeo Taguchi

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

In the presence of the Trost ligands-Pd catalysts, N-monoallylation of bis(2,4,6-triisopropylbenzne)sulfonylamides derived from meio-1,2-diamines proceeds with good to excellent enantioselectivity (85-96% ee) to give asymmetric desymmetrization products. Under the same conditions, in the reaction with meso-bistolunesulfonylamide derivatives, reversal of the enantioselectivity is observed.

Original languageEnglish
Pages (from-to)2524-2527
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number6
DOIs
Publication statusPublished - 2006 Mar 17
Externally publishedYes

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Allylation
Diamide
Enantioselectivity
Derivatives
Catalysts
Diamines
Ligands

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Catalytic asymmetric desymmetrization of meso-diamide derivatives through enantioselective N-allylation with a chiral π-allyl Pd catalyst : Improvement and reversal of the enantioselectivity. / Kitagawa, Osamu; Matsuo, Shinichi; Yotsumoto, Kanako; Taguchi, Takeo.

In: Journal of Organic Chemistry, Vol. 71, No. 6, 17.03.2006, p. 2524-2527.

Research output: Contribution to journalArticle

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