The Journal of Organic Chemistry

Cross Coupling of Alkyl Cobaloximes with Maleic Anhydrides. Basic Studies and Applications to the Synthesis of Chaetomellic Acid A Anhydride and C-Glycosyl …

RM Slade, BP Branchaud

Index: Slade, Rachel M.; Branchaud, Bruce P. Journal of Organic Chemistry, 1998 , vol. 63, # 11 p. 3544 - 3549

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Citation Number: 23

Abstract

Abstract: Photochemical cross coupling of alkyl cobaloximes with maleic anhydrides and PhSSPh led to addition of an alkyl moiety and an SPh moiety across the alkene. Oxidation of the sulfide to a sulfoxide followed by elimination of phenyl sulfenic acid provided substituted maleic anhydrides. Alkyl cobaloximes could also be coupled with maleic anhydrides in the absence of PhSSPh to provide substituted maleic anhydrides directly. These methods are ...