441351-66-2Relevant academic research and scientific papers
Highly chemoselective Pummerer reactions of sulfinyldiacetic acid derivative
Nagao, Yoshimitsu,Miyamoto, Satoshi,Hayashi, Kazuhiko,Mihira, Ado,Sano, Shigeki
, p. 1519 - 1522 (2002)
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.
Synthesis of new chiral sulfinyldiacetic acid derivatives and attempt at chemoselective asymmetric pummerer reaction
Nagao, Yoshimitsu,Miyamoto, Satoshi,Hayashi, Kazuhiko,Mihira, Ado,Sano, Shigeki
, p. 558 - 562 (2007/10/03)
(RS)-1 (85% ee) was prepared by utilizing a porcin pancreatic lipase-promoted hydrolysis of sulfinyldiacetic acid dimethyl ester (8) which was derived from thiodiacetic acid (7). (RS)-1 (99% ee) and (S S)-1 (99% ee) were r
