R-sulconazole

SCHEME 14.9. Enantioselective synthesis of (R)-sulconazole involving the asymmetric addition of thioacetic acid to a nitroalkene, catalyzed by 15, as the key step. 

New applications demanded changes in catalyst structure. The steric bulk around the sulfur atom was increased and a tertiary amine function was introduced on a cyclohexyl framework in catalyst 37 to efficiently promote the addition reactions ofthioacetic acid to nitroalkenes [139]. The general procedure developed here was applied as the key asymmetric step in the synthesis of (R)-sulconazole (32% overall yield for five steps, 96% ee). A very similar catalyst was used in the... 

Scheme 34.11 Synthesis of (R)-sulconazole through organocatalyzed sulfa-Michael.

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