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Volumn 339, Issue 6, 1997, Pages 541-546

A new enantioselective synthetic approach to β-aminothio-compounds via enantioselective reduction of N,S-heterocyclic imines

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EID: 0001644332     PISSN: 09411216     EISSN: None     Source Type: Journal    
DOI: 10.1002/prac.19973390197     Document Type: Article
Times cited : (10)

References (39)
  • 10
    • 2742591090 scopus 로고
    • Eur. Pat. 33919
    • b) K. J. M. Andrews, Eur. Pat. 33919; Chem. Abstr. 96 (1982) 52498;
    • (1982) Chem. Abstr. , vol.96 , pp. 52498
    • Andrews, K.J.M.1
  • 12
    • 0030591837 scopus 로고    scopus 로고
    • In parallel and indepently from our research the enantioselective C=N-reduction of a further thiocontaining heterocycle (a pyrrolo-benzothiadiazine derivative) was reported recently, see: P. D. P, Serkiz, P. Morain, J. Lepagnol, A. Cordy, Bioorg. Med. Chem. Lett. 6 (1996) 3003
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 3003
    • Serkiz, P.D.P.1    Morain, P.2    Lepagnol, J.3    Cordy, A.4
  • 16
    • 84982076854 scopus 로고
    • For the reduction of 3-thiazolines with achiral reducing agents in general, see: M. Thiel, F. Asinger, K. Häussler, T. Körner, Liebigs Ann. Chem. 622 (1959) 107 (however, the thiazolines 1a,b are new and have not been reduced before)
    • (1959) Liebigs Ann. Chem. , vol.622 , pp. 107
    • Thiel, M.1    Asinger, F.2    Häussler, K.3    Körner, T.4
  • 17
    • 0026679821 scopus 로고
    • Until now only several acyclic imines were reduced via this method using stoichiometric amounts of chiral agents, see: B. T. Cho, Y. S. Chun, Tetrahedron: Asymmetry 3 (1992) 1583
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1583
    • Cho, B.T.1    Chun, Y.S.2
  • 22
    • 37049111060 scopus 로고    scopus 로고
    • 1H NMR spectra of the crude product showed for the resulting diastereomers nonequivalence of the CH-OAc singlet with Δδ = 0.22 ppm in case of 2 (signals at δ = 6.10 ppm and 6.32 ppm) and nonequivalence of the CH(Ph)N singlet with Δδ = 0.03 ppm in case of 12 (signals at δ = 4.24 ppm and 4.27 ppm). For the procedure of this CDA-derivatization method, see: a) D. Parker, J. Chem. Soc.; Perkin Trans. II 1983 83;
    • J. Chem. Soc.; Perkin Trans. II , vol.1983 , pp. 83
    • Parker, D.1
  • 29
    • 0018825393 scopus 로고
    • 1H NMR spectra (resonances for CHPh were centered at δ = 4.48 ppm and 5.05 ppm). For this CDA-derivatization method, see: K. C. Rice, A. Brossi, J. Org. Chem. 45 (1980) 592
    • (1980) J. Org. Chem. , vol.45 , pp. 592
    • Rice, K.C.1    Brossi, A.2
  • 32
    • 2742583530 scopus 로고
    • Chem. Abstr. 79 (1973) 126422
    • (1973) Chem. Abstr. , vol.79 , pp. 126422
  • 37
    • 0000473171 scopus 로고
    • for characterization, see ref. [17]
    • The synthesis of rac-14 was carried out by catecholborane reduction (method C). However, an alternative route to rac-14 was reported earlier in: P. Marchini, G. Liso, A. Reho, J. Org. Chem. 40 (1975) 3453 (for characterization, see ref. [17])
    • (1975) J. Org. Chem. , vol.40 , pp. 3453
    • Marchini, P.1    Liso, G.2    Reho, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.