A new sulfenylation reagent, 3-phenylsulfenyl-2-(N- cyanoimino)thiazolidine, and its optically active version

Synlett

Volumn , Issue 1, 2000, Pages 33-36

  Tanaka, T ^a   Azuma, T ^a   Fang, X ^a   Uchida, S ^a   Iwata, C ^a   Ishida, T ^a   In, Y ^a   Maezaki, N ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

3 phenylsulfenyl 2 (N cyanoimino)thiazolidine; Asymmetric sulfenylation; Asymmetrical disulfide; Sulfenamide

Indexed keywords

AMINE; DISULFIDE; SULFENAMIDE DERIVATIVE; THIAZOLIDINE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033977223     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

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8. Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Synthesis 1988, 261-262; Iwata, C.; Fujimoto, M.; Okamoto, S.; Nishihara, C.; Sakae, M.; Katsurada, M.; Watanabe, M.; Kawakami, T.; Tanaka,T.; Imanishi, T. Heterocycles 1990, 31, 1601-1604; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Maeda, N.; Imanishi, T.; Tanaka, T. Heterocycles 1991, 52, 2471-2478; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Nakamoto, Y.; Sakae, M.; Katsurada, M.; Imanishi, T.; Tanaka, T. J. Chem. Soc., Chem. Commun. 1992, 1379-1381; Tanaka, T.; Watanabe, M.; Nakamoto, Y.; Okuno, K.; Maekawa, K.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 2301-2302; Tanaka, T.; Nakamoto, Y.; Maekawa, K.; Watanabe, M.; Nishihara, C; Iwata, C. Heterocycles 1996, 42, 265-272; Tanaka, T.; Takase, W.; Xie, F.; Azuma, T.; Uchida, S.; Ishida, T.; In, Y.; Iwata, C. Synlett 1997, 316-318.
9. Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Synthesis 1988, 261-262; Iwata, C.; Fujimoto, M.; Okamoto, S.; Nishihara, C.; Sakae, M.; Katsurada, M.; Watanabe, M.; Kawakami, T.; Tanaka,T.; Imanishi, T. Heterocycles 1990, 31, 1601-1604; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Maeda, N.; Imanishi, T.; Tanaka, T. Heterocycles 1991, 52, 2471-2478; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Nakamoto, Y.; Sakae, M.; Katsurada, M.; Imanishi, T.; Tanaka, T. J. Chem. Soc., Chem. Commun. 1992, 1379-1381; Tanaka, T.; Watanabe, M.; Nakamoto, Y.; Okuno, K.; Maekawa, K.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 2301-2302; Tanaka, T.; Nakamoto, Y.; Maekawa, K.; Watanabe, M.; Nishihara, C; Iwata, C. Heterocycles 1996, 42, 265-272; Tanaka, T.; Takase, W.; Xie, F.; Azuma, T.; Uchida, S.; Ishida, T.; In, Y.; Iwata, C. Synlett 1997, 316-318.
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18. Physical data of 3: Colorless crystals, mp. 86-87°C (hexane-AcOEt). 1H NMR (CDCl3) δ: 3.40 (2H, t, J = 7.3 Hz), 4.10 (2H, t, J = 7.3 Hz), 7.36-7.50 (5H, Ar-H). 13C NMR (CDCl3) δ: 27.5, 56.8, 116.2, 129.5 (× 3), 129.8 (× 2), 133.6, 178.8. MS m/z:235(M+), 109 (base).
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29. Et3SiH with trifluoroacetic acid gave no desired product. Birch reduction gave 10 around 40% yield.
30. Physical data of 4: Colorless crystals, mp. 85-87°C (benzene). [α]D25+55.6 (c = 0.970, CHCl3). 1H NMR (CDCl3) δ: 3.26 (1H, dd, J = 2.4, 11.6 Hz), 3.62 (1H, dd, J = 7.9, 11.6 Hz), 4.66 (1H, d, J = 7.9 Hz), 4.84 (1H, ddd, J = 2.4, 7.9, 7.9 Hz), 7.18-7.39 (15H, m). 15C NMR (CDCl3) δ: 32.1, 52.5, 70.5, 116.0, 127.5, 127.7, 128.2 (× 2), 128.4, 128.7 (× 2), 128.9 (× 2), 129.0 (× 2), 129.1 (× 2), 129.5 (× 2), 135.1, 139.0, 139.2, 178.8. MS m/z: 402 (M++H, base). Crystal data of 4: C23H19N3S2•C6H 6, Mr = 479.66, orthorhombic, space group P2I2I2I, Cell constant a (Å) = 11.496 (3), b (Å) = 26.268 (4), c (Å) = 8.605 (3), α (°) = 90.00, β(°) = 90.00 (1), γ (°) = 90.00, Volume (Å3) = 2598 (1), Z = 4, Dx = 1.226 g cm-3, μ(Cu-Kα)(mm-1) = 2.01, R = 0.040, RW = 0.132.
31. The optical purity was determined as follows. The carbonyl group of α-phenylthio-β-keto compound was reduced by NaBH4 to give two diastereomeric alcohols, one of which was converted to MTPA ester and then analyzed by NMR measurement.
32. The absolute configuration of the β-keto methyl ester was determined by an X-ray crystallographic analysis of an acetal derived from the keto ester and (R,R)-2,3-butanediol. Crystal data; C18H24O4S, Mr = 336.43, orthorhombic, space group P2I2I2I, Cell constant a (Å) = 12.305 (1), b (Å) = 15.260 (1), c (Å) = 9.655 (1), α (°) = 90.00, β(°) = 90.00 (1), γ (°) = 90.00, Volume (Å) = 1812.9 (2), Z = 4, Dx = 1.233 g cm-3, μ(Cu-Kα)(mm-1) = 1.73, R = 0.035, RW= 0.104.