Microwave-Assisted Regioselective Synthesis of trans-1-Arenesulfonyl-2-ethoxycarbonyl-3-phenylazetidines

Abstract

An efficient regioselective synthesis of trans-1-arenesulfonyl-2-ethoxycarbonyl-3-phenylazetidines has been achieved through microwave-assisted reactions of 1-arenesulfonylaziridines with dimethylsulfonium carboethoxymethylide using alumina as solid support.

Keywords:

• 1-Arenesulfonylaziridines
• dimethylsulfonium carboethoxymethylide
• microwave
• regioselective
• trans-1-arenesulfonyl-2-ethoxycarbonyl-3-phenylazetidines

ACKNOWLEDGMENTS

We thank the Council of Scientific and Industrial Research (CSIR), New Delhi, for fellowships to S. M. and D. S. T., New Delhi for funding a single-crystal diffractometer under the Funding for Infrastructure in Science and Technology program to the Department of Chemistry, Indian Institute of Technology, Delhi. We also thank J. Thomas for collecting the X-ray data and S. Upreti and M. S. Kumar for their help in the crystallographic analysis.

Notes

^a All reactions were carried out on Al₂O₃, initially at 160 W/5 min/90 °C and then at 320 W/2 min/110 °C.

^b Products were characterized by NMR, IR, and HRMS.

^c Isolated, unoptimized yields.

Author Upender K. Nadir is deceased (September 27, 2007).