Catalytic Enantioselective Synthesis of N-C Axially Chiral Sulfonamides through Chiral Palladium-Catalyzed N-Allylation

Yuki Kikuchi, Chisato Nakamura, Mizuki Matsuoka, Rina Asami, Osamu Kitagawa

Research output: Contribution to journalArticle

Abstract

In the presence of (S,S)-Trost ligand and (allyl-Pd-Cl)2 catalyst, the reaction of allyl acetate with the anionic species prepared from various N-(2-tert-butylphenyl)sulfonamides and NaH proceeded in an enantioselective manner (up to 95% ee) to give optically active N-allylated sulfonamide derivatives possessing an N-C axially chiral structure in high yields.

Original languageEnglish
Pages (from-to)8112-8120
Number of pages9
JournalJournal of Organic Chemistry
Volume84
Issue number12
DOIs
Publication statusPublished - 2019 Jun 21

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Allylation
Sulfonamides
Palladium
Ligands
Derivatives
Catalysts

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Catalytic Enantioselective Synthesis of N-C Axially Chiral Sulfonamides through Chiral Palladium-Catalyzed N-Allylation. / Kikuchi, Yuki; Nakamura, Chisato; Matsuoka, Mizuki; Asami, Rina; Kitagawa, Osamu.

In: Journal of Organic Chemistry, Vol. 84, No. 12, 21.06.2019, p. 8112-8120.

Research output: Contribution to journalArticle

Kikuchi, Yuki ; Nakamura, Chisato ; Matsuoka, Mizuki ; Asami, Rina ; Kitagawa, Osamu. / Catalytic Enantioselective Synthesis of N-C Axially Chiral Sulfonamides through Chiral Palladium-Catalyzed N-Allylation. In: Journal of Organic Chemistry. 2019 ; Vol. 84, No. 12. pp. 8112-8120.
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