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Paper | Special issue | Vol 74, No. 1, 2007, pp.827-834
Published online, 26th November, 2007
DOI: 10.3987/COM-07-S(W)74
Pd(II)-Catalyzed Enantioselective Intramolecular Heck-Type Reaction to Construct Chiral Sulfonamide Rings

Katsuhiro Akiyama and Koichi Mikami*

*Department of Applied Chemistry, Graduate School of Science and Technology, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan

Abstract

The first example of enantioselective intramolecular Heck-type reaction to construct chiral quaternary carbon centers of sulfonamide rings is reported. The reaction provides the expected Heck products along with the unexpected olefin reduction products. We discovered the catalyst prepared from (S,S)-chiraphos and Pd2dba3 to afford the products in high yields and enantioselectivities up to 86% ee at room temperature. Deuterated solvent and base are also examined to elucidate the mechanism of reduction of olefin. Pd hydride species produced from β-elimination are responsible for olefin reduction.