Synthesis of 1,3-oxathiolane sulfoxide compounds

Details Synthesis of 1,3-oxathiolane sulfoxide compounds Synthesis of 1,3-oxathiolane sulfoxide compounds

C - Chemistry, Metallurgy

07

D

C07D 327/04 (2006.01) C07D 327/02 (2006.01) C07D 327/06 (2006.01)

Patent

CA 2183714

A process for the production of a 1,3-oxathiolane sulfoxide of the formula <see formula I> wherein X is an amino group of the formula -NHR, wherein R is hydrogen, phenyl, C1 - C8 alkyl, C3 - C6 cycloalkyl, nitrophenyl, (C1 - C4 alkoxy)phenyl, furfuryl, halophenyl, tolyl, napthyl, biphenyl or hydroxyphenyl; or X is an alkoxy group of the formula -OR' wherein R is C1 - C6 alkyl, which process comprises oxidizing a 1,3-oxathiolane of the formula <see formula IA> wherein X is as defined above, in the presence of an effective amount of aqueous hydrogen peroxide and a sterically-hindered organoselenium compound of the formula Image or R2-Se-Se-R2 wherein R2 is aryl, mono-, di- or tri-substituted with C1 - C3 alkyl, to the produce the 1,3-oxathiolane sulfoxide. This process stereoselectively produces the cis stereoisomer of the 1,3-oxathiolane sulfoxide. Additionally, there is disclosed a novel method for the preparation of 5,6-dihydro-2-methyl-1,4- oxathiin compounds using this process.

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