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Synlett 2000; 2000(1): 33-36
DOI: 10.1055/s-2000-6471
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A New Sulfenylation Reagent, 3-Phenylsulfenyl-2-(N-cyanoimino)thiazolidine, and Its Optically Active Version

Tetsuaki Tanaka* , Tsutomu Azuma, Xie Fang, Shuji Uchida, Chuzo Iwata, Toshimasa Ishida, Yasuko In, Naoyoshi Maezaki
  • *Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan; Fax + 81 6 6879 8214; E-mail: t-tanaka@phs.osaka-u.ac.jp
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Publication Date:
31 December 2000 (online)

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We have developed a new sulfenylation reagent, 3-phenylsulfenyl-2-(N-cyanoimino)thiazolidine 3, that is readily available and stable upon storage. Compound 3 easily reacts with amines or thiols to give the corresponding sulfenamides or asymmetrical disulfides in excellent yields. It was also found that the α-sulfenylation reaction of carbonyl compounds with 3 proceeds smoothly. Furthermore, optically active 4-diphenylmethyl derivative 4 was synthesized as an asymmetric sulfenylation reagent, which realized 96% e.e. upon α-sulfenylation of a cyclic β-keto ester.

sulfenamide - asymmetrical disulfide - asymmetric sulfenylation - 3-phenylsulfenyl-2-(N-cyanoiomino)thiazolidine

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