Organophosphorus compounds VII: The absolute configuration of sarin and related anticholinesterases established by chemical correlation

HP Benschop, GR Van den Berg…

Index: Benschop,H.P. et al. Recueil des Travaux Chimiques des Pays-Bas, 1968 , vol. 87, p. 387 - 395

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Citation Number: 28

Abstract

Abstract The reaction of (+)-(i-PrO) MeP (O) SMe with phenylmagnesium bromide in tetrahydrofuran affords (+)-(i-PrO) MeP (O) Ph, representing the first example of a stereospecific synthesis of a phosphinate ester from a phosphonothiolate ester. Levorotatory (MeS) MeP (O) Ph is converted into (R)-(+)-n-PrMeP (O) Ph with inversion of configuration by reaction with n-propylmagnesium bromide. The two Grignard reactions are correlated ...