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A STUDY OF ATYPICAL REACTION OF METHYL (TRIPHENYLPHOSPHORANYLIDENE)ACETATE WITH 3a-SUBSTITUTED BICYCLIC β-KETO-γ-SULTAMS

Taras V. Omelian, Pavlo O. Iegorov, Anton O. Poliudov, Alexey V. Dobrydnev, Eugeniy N. Ostapchuk, Yulian M. Volovenko
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Abstract


A number of 2-substituted 4–7-membered cyclic amino acid esters bearing endocyclic amino group were sequentially mesylated and cyclized via the CSIC reaction strategy to give the key precursors 3a-substituted bicyclic isothiazolidin-4-one 1,1-dioxides. Further reaction with methyl (triphenylphosphoranylidene)acetate afforded the corresponding 3a-substituted 2-[(triphenylphosphonio)acetyl]perhydro[1,2]thiazoloazahetaryl-3-olate 1,1-dioxides. The nature of the substituent at position 3a plays a crucial role in the reaction direction with this Wittig reagent. Specifically, 3a-unsubstituted counterpart participates in the classical course of the reaction providing the expected prototropic mixture of corresponding esters.

Keywords


amino acids; phosphonium ylides; sulfonamides; acylation; CSIC reaction; cyclization; Wittig reaction.

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