Synthesis of New Chiral Sulfinyldiacetic Acid Derivatives and Attempt at Chemoselective Asymmetric Pummerer Reaction

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概要

• 論文の詳細を見る

• (R_s)-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). (R_s)-1 (99% ee) and (S_s)-1 (99% ee) were readily obtained by methanolysis of (R_s,S)-12 and (S_s,S)-12 with MeONa in MeOH. (R_s,S)-12 and (S_s,S)-12 were furnished by chromatographic separation of the diastereomeric mixture, obtained by oxidation of thiodiacetic mono-carboxylic acid (11) with 30% H_2O_2 followed by dehydrative condensation of the resultant sulfinyldiacetic mono-carboxylic acid with 4(S)-isopropyl-1,3-thiazolidine-2-thione. (R_s)-1 (99% ee) was successively treated with (TMS)_2NLi, Ac_2O, and TMSOTf to give a major chiral-3 product in 75% ee and in a highly chemoselective manner (chiral-3 : chiral-2=93 : 7).

• 社団法人日本薬学会の論文
• 2002-04-01

著者

• HAYASHI Kazuhiko

  Faculity of Pharmaceutical Sciences, The University of Tokushima

• NAGAO Yoshimitsu

  Faculity of Pharmaceutical Sciences, The University of Tokushima

• MIYAMOTO Satoshi

  Faculty of Pharmaceutical Sciences, The University of Tokushima

• MIHIRA Ado

  Faculty of Pharmaceutical Sciences, The University of Tokushima

• SANO Shigeki

  Faculty of Pharmaceutical Sciences, The University of Tokushima

• 佐野 茂樹

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• 佐野 茂樹

  徳島大学薬学部

• Hayashi Kyoko

  Faculty Of Medicine Toyama Medical And Pharmaceutical University

• Mihira Ado

  Faculty Of Pharmaceutical Sciences The University Of Tokushima

• 長尾 善光

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• 長尾 善光

  徳島大学薬学部

• Nagao Y

  Faculty Of Pharmaceutical Sciences The University Of Tokushima

• Nagao Yoshimitsu

  Faculity Of Pharmaceutical Sciences The University Of Tokushima

• Miyamoto S

  Faculty Of Pharmaceutical Sciences The University Of Tokushima

• Miyamoto Satoshi

  Faculty Of Engineering Ibaraki University

• Hayashi K

  Graduate School Of Medicine And Pharmaceutical Sciences For Research University Of Toyama

• Mihira A

  Faculty of Pharmaceutical Sciences, The University of Tokushima

• Sano S

  Faculty of Pharmaceutical Sciences, The University of Tokushima

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