Studies on the stereoselective methylation of. ALPHA.-sulfinyl carbanions generated from three isomeric pyridylmethyl p-tolyl sulfoxides and benzyl 2-pyridyl sulfoxide.

N Furukawa, E Hosono, H Fujihara…

Index: Furukawa; Hosono; Fujihara; Ogawa Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 2 p. 461 - 465

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Citation Number: 11

Abstract

A high stereoselectivity in the methylation of 2-pyridylmethyl p-tolyl sulfoxide (2a) with lithium diisopropylamide and iodomethane was observed at low temperature. The chelation of Li+ by both the nitrogen atom in the pyridine ring and the sulfinyl oxygen atom in 2a promotes the stereoselectivity as compared with isomeric sulfoxides.

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