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Communication | Regular issue | Vol 32, No. 4, 1991, pp.679-684
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5691
Role of Heterocycles on the Stereoselective Reactions of α-Sulfinyl Carbanions Using Optically Active 2-Pyridylmethyl p-Tolyl and 2-(N-Methylimidazolyl)methyl p-Toyl Sulfoxides with Aldehydes

Naomichi Furukawa,* Takahiro Sagae, and Satoshi Ogawa

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan

Abstract

Optically active 2-pyridylmethyl p-tolyl (1) and 2-(N-methylimidazolyl)methyl p-tolyl sulfoxides (2) were synthesized and the reactions of their chiral α-sulfinyl carbanions with aldehydes afforded stereoselectively the condensation products. The absolute configurations of the products were determined by X-ray crystallographic analysis and chemical reactions. The mechanism for the reactions is described.