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Paper | Special issue | Vol 62, No. 1, 2004, pp.263-277
Published online, 27th May, 2003
DOI: 10.3987/COM-03-S(P)6
Geometrically Selective Synthesis of Sulfur-containing Heterocycles by Intramolecular Pd-catalyzed Sulfinylzincation

Naoyoshi Maezaki,* Suguru Yagi, Jun Maeda, Ryoko Yoshigami, and Tetsuaki Tanaka*

*Graduate School of Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan

Abstract

A new method to synthesize cyclic sulfoxide derivatives was developed utilizing Pd-catalyzed sulfinylzincation, which proceeds with high syn-selectivity under mild conditions. The resulting vinylzinc species reacted with electrophiles such as proton, allyl bromide, and benzoyl chloride to afford a single geometric isomer.