Abstract
Sulfinyldiacetic acid amide ester rac- 1 was efficiently synthesized starting from thiodiacetic acid 4 . Treatment of rac- 1 with Ac 2O and TMSOTf in CH 2Cl 2 at −40°C gave chemoselectively amide site α-acetoxy sulfide rac- 2 in a ratio (91:9) of rac- 2 and rac- 3 and in a 90% total yield. Similar treatment of 1 with Ac 2O and TMSOTf in DMF at room temperature furnished ester site α-acetoxy sulfide rac- 3 in a highly chemoselective manner ( rac- 2 : rac- 3 =3:97) and in a 92% total yield.
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