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

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2024 Sep 30

PMID 39348273

Authors

Kayambu Namitharan

Torsten Cellnik

Assel Mukanova

Shinwon Kim

Alan R Healy

Affiliations

Soon will be listed here.

Abstract

Herein, we demonstrate that the enhanced electrophilicity of -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 -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.

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

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