Synthesis of 4-trifluoromethyl-β-sultams via sulfa-Staudinger cycloadditions

ABSTRACT

A series of structurally diverse 4-trifluoromethyl β-sultams was conveniently synthesized via the sulfa-Staudinger cycloadditions of 2,2,2-trifluoroethanesulfonyl chloride with different imines under very mild conditions. The products were obtained in yields up to 75%, and in cis/trans ratios ranging from 59:41 to 12:78.

GRAPHICAL ABSTRACT

KEYWORDS:

• Sultam
• Sulfa-Staudinger cycloaddition
• sulfene
• imine
• annulation

Acknowledgment

This work was supported by the National Natural Science Foundation of China (No. 21602010, to Z. H. Yang) and (No. 21372025, to J. X. Xu), the BUCT Fund for Discipline Construction and Development (Project No. XK1533, to Z. Yang), and the China Postdoctoral Science Foundation (No. 2016M600900, to Z. Yang).

Surporting information

Copies of ¹H, ¹³C and ¹⁹F NMR spectra of products, copies of ¹⁹F NMR spectra of crude reaction mixtures in reaction condition optimization, and copies of ¹H NMR spectra of crude reaction mixtures in substrate scope extension.