Chiral functionalization of 2(3H)-thiazolone. New route to chiral synthons for 2-amino thiols~

摘要

Treatment of 3-[2-(R)-methoxyethoxy- or 3-[2-(R)-methoxyethoxyethoxy-7,7-dimethylbicyclo[2.2.1]heptane-1(S)-carbonyl]-2-thiazolones with Br_2 / MeC(OMe)_3 and C_6H_5SeCl/ MeOH resulted in the diastereoselective formation of 4(S)-methoxy-5(S)-bromo- and 4(R)-methoxy-5(R)-phenylseleno-2-thiazolidinones, respectively, with high to excellent pi-facial selectivity, but with opposite diastereofacial selection. The adducts thus obtained are potentially useful as chiral synthons for 2-amino thiols.