Work

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

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c03139

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

Institution: New York University Abu Dhabi

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: New York University Abu Dhabi