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Volumn 69, Issue 12, 2004, Pages 4227-4237

New resolution of 2-formyl-1,4-DHP derivatives using CIDR methodology. Facile access to new chiral tricyclic thiolactam

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CRYSTALLIZATION; DERIVATIVES; HYDROLYSIS; SOLUBILITY; SOLUTIONS;

EID: 2942560555     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049706s     Document Type: Article
Times cited : (20)

References (63)
  • 23
    • 2942617305 scopus 로고    scopus 로고
    • note
    • The starting material, 1,4-DHP derivative 4, could be obtained in large scale-up to 20 g in a single preparative step.
  • 24
    • 0030342797 scopus 로고    scopus 로고
    • and references therein
    • (a) For recent review related to this subject, see: Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447 and references therein.
    • (1996) Chem. Soc. Rev. , vol.25 , pp. 447
    • Caddick, S.1    Jenkins, K.2
  • 25
    • 2942583791 scopus 로고    scopus 로고
    • note
    • (b) For recent examples, see:
  • 28
    • 2942583536 scopus 로고    scopus 로고
    • note
    • The proximity of a chiral auxiliary to the labile stereocenter in the crystallization process is sometimes no as important. See ref bellow 14.
  • 29
    • 2942524006 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for the ORTEP drawing of the enantiopures imines (4S,1′R)-6 and (4S,1′R)-6.
  • 32
    • 2942613245 scopus 로고    scopus 로고
    • note
    • (a) For the X-ray single-crystal structure determination of (4S,2′R,4′R)-9, see the crystallographic characteristics in the Supporting Information (SI1).
  • 40
    • 0025063283 scopus 로고
    • and references therein
    • For example of spectroscopic study on 1,3-thiazoles, see: Fülöp, F.; Mattinen, J.; Pihlaja, K. Tetrahedron 1990, 46, 6545 and references therein.
    • (1990) Tetrahedron , vol.46 , pp. 6545
    • Fülöp, F.1    Mattinen, J.2    Pihlaja, K.3
  • 50
    • 2942553833 scopus 로고    scopus 로고
    • note
    • For the X-ray single-crystal structure determination of (4S,2′S,4′R)-15, see the crystallographic characteristics in the Supporting Information.
  • 52
    • 0025992651 scopus 로고
    • The oxygenated heterologues of these tricyclic lactams were elegantly and fully exploited by numerous groups, notably by Meyers. For more information, see the following reviews: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503.
    • (1991) Tetrahedron , vol.47 , pp. 9503
    • Romo, D.1    Meyers, A.I.2
  • 54
    • 2942613244 scopus 로고    scopus 로고
    • note
    • For the X-ray single-crystal structure determination of (±)-(6R,-9bR)-21, see the crystallographic characteristics in the Supporting Information.
  • 55
    • 2942553832 scopus 로고    scopus 로고
    • note
    • For the X-ray single-crystal structure determination of (4R,2′S)-20, see the crystallographic characteristics in the Supporting Information.
  • 60
    • 0014489596 scopus 로고
    • Substitution of the phenyl ring of cephalexin with certain substituents does not appear to modify significantly the antibacterial properties of cephalexin (R = H). For more information, see: Ryan, C. W.; Simon, R. L.; Van Heyningen, E. M. J. Med. Chem. 1969, 12, 310.
    • (1969) J. Med. Chem. , vol.12 , pp. 310
    • Ryan, C.W.1    Simon, R.L.2    Van Heyningen, E.M.3
  • 63
    • 4243416950 scopus 로고
    • Japanese Patent. FR 2,315,930, 1977; US 4,145,432, 1977
    • Yoshinari, S.; Japanese Patent. FR 2,315,930, 1977; US 4,145,432, 1977; Chem. Abstr. 1977, 86, 189726.
    • (1977) Chem. Abstr. , vol.86 , pp. 189726
    • Yoshinari, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.