A Dual Role for the N-Perfluorobutanesulfinamide Auxiliary in an Asymmetric Decarboxylative Mannich Reaction

Kayambu Namitharan, Torsten Cellnik, Assel Mukanova, Shinwon Kim, Alan R. Healy

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, we demonstrate that the enhanced electrophilicity of N-perfluorobutanesulfinamide auxiliary-derived imines enables a highly selective decarboxylative Mannich reaction under mild conditions. The molecular sieves-mediated transformation tolerates a broad substrate scope and produces chiral β-amino thioesters in high yield. Additionally, we demonstrate that the N-perfluoroalkyl sulfinyl group can function as a phase tag for fluorous purification, thus enabling the rapid isolation of the chiral amine products by solid-phase extraction. The synthetic utility of this method is illustrated by the synthesis of sitagliptin, ruspolinone, and the natural product negamycin.

Original languageEnglish (US)
JournalOrganic Letters
DOIs
StateAccepted/In press - 2024

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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