Title of article :
Highly chemoselective Pummerer reactions of sulfinyldiacetic acid derivative
Author/Authors :
Nagao، نويسنده , , Yoshimitsu and Miyamoto، نويسنده , , Satoshi and Hayashi، نويسنده , , Kazuhiko and Mihira، نويسنده , , Ado and Sano، نويسنده , , Shigeki، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2002
Abstract :
Sulfinyldiacetic acid amide ester rac-1 was efficiently synthesized starting from thiodiacetic acid 4. Treatment of rac-1 with Ac2O and TMSOTf in CH2Cl2 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 Ac2O 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.
Keywords :
Lewis acid , solvents and solvent effects , sulfoxides , Chemoselectivity , Pummerer reactions
Journal title :
Tetrahedron Letters
Journal title :
Tetrahedron Letters
