The Journal of Organic Chemistry

Stereospecific reductive desulfurization of vinyl sulfoxides with tert-butyllithium and an internal proton source

PG Theobald, WH Okamura

Index: Theobald, Paula G.; Okamura, William H. Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 741 - 750

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Citation Number: 52

Abstract

Trienyl and allenyl phenyl sulfoxides can be reduced stereospecifically with retention of configuration in good yields using tert-butyllithium with methanol (MeOH) as an internal (in situ) proton source. The method can be easily modified to give stereospecifically deuterium- labeled compounds. While simple monoene sulfoxides afford attenuated yields of reduced olefin, the method is useful for the reduction of the more sensitive and complex polyene ...

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