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

DOI: 10.1246/bcsj.63.461

Source and publish data:

Bulletin of the Chemical Society of Japan p. 461 - 465 (1990)

Update date:2022-08-04

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Authors:

Furukawa

Hosono Hosono

Fujihara

Ogawa Ogawa

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Article abstract of DOI:10.1246/bcsj.63.461

A high stereoselectivity in the methylation of 2-pyridylmethyl p-totyl 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.

Full text of DOI:10.1246/bcsj.63.461

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