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Volumn 72, Issue 12, 2007, Pages 4431-4439

Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOIDS; LACTAM; SUBSTITUENTS;

EID: 34250195722     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070397q     Document Type: Article
Times cited : (74)

References (42)
  • 1
    • 0025992651 scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503.
    • (1991) Tetrahedron , vol.47 , pp. 9503
    • Romo, D.1    Meyers, A.I.2
  • 2
    • 0004157026 scopus 로고
    • Trost, B. M, Ed, Blackwell Scientific Publications: Oxford
    • (b) Meyers, A. I. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed.; Blackwell Scientific Publications: Oxford, 1994; pp 145-175.
    • (1994) Stereocontrolled Organic Synthesis , pp. 145-175
    • Meyers, A.I.1
  • 20
    • 34250204040 scopus 로고    scopus 로고
    • The absolute configuration of the dialkylated lactams 9a and 10a was unambiguously confirmed by X-ray crystallographic analysis.
    • The absolute configuration of the dialkylated lactams 9a and 10a was unambiguously confirmed by X-ray crystallographic analysis.
  • 21
    • 0035215106 scopus 로고    scopus 로고
    • For the synthesis of enantioenriched (ee = 42%) lactam 15 by asymmetric dialkylation of a chiral N-(dialkylamino)lactam, see: Enders, D.; Teschner, P.; Raabe, G.; Runsink, J. Eur. J. Org. Chem. 2001, 4463.
    • For the synthesis of enantioenriched (ee = 42%) lactam 15 by asymmetric dialkylation of a chiral N-(dialkylamino)lactam, see: Enders, D.; Teschner, P.; Raabe, G.; Runsink, J. Eur. J. Org. Chem. 2001, 4463.
  • 28
    • 0024338679 scopus 로고    scopus 로고
    • (-)-Quebrachamine was also obtained, although in poorer yield (5%), when the reduction was carried out with BH3 in THF at reflux, following the conditions reported for the complete reduction of related seven-membered keto lactams: Khandelwal, Y.; Jain, P. C.; Anand, N. Indian J. Chem. B 1989, 28B, 475.
    • (-)-Quebrachamine was also obtained, although in poorer yield (5%), when the reduction was carried out with BH3 in THF at reflux, following the conditions reported for the complete reduction of related seven-membered keto lactams: Khandelwal, Y.; Jain, P. C.; Anand, N. Indian J. Chem. B 1989, 28B, 475.
  • 31
    • 0003409081 scopus 로고    scopus 로고
    • 4 reduction of related tetracyclic nine-membered 16-oxolactams, see: (a) Narisada, M.; Watanabe, F.; Nagata, W. Tetrahedron Lett. 1971, 39, 3681.
    • 4 reduction of related tetracyclic nine-membered 16-oxolactams, see: (a) Narisada, M.; Watanabe, F.; Nagata, W. Tetrahedron Lett. 1971, 39, 3681.
  • 32
    • 0015941016 scopus 로고    scopus 로고
    • Ziegler, F. E.; Bennett, G. B. J. Am. Chem. Soc. 1973, 95, 7458. See also ref 5.
    • (b) Ziegler, F. E.; Bennett, G. B. J. Am. Chem. Soc. 1973, 95, 7458. See also ref 5.
  • 38
    • 37049096415 scopus 로고
    • For previous enantioselective syntheses of the alkaloids, and, )-quebrachamine, see: a
    • For previous enantioselective syntheses of the alkaloids (+)- and (-)-quebrachamine, see: (a) Takano, S.; Chiba, K.; Yonaga, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1980, 616.
    • (1980) J. Chem. Soc., Chem. Commun , pp. 616
    • Takano, S.1    Chiba, K.2    Yonaga, M.3    Ogasawara, K.4
  • 41
    • 0036134459 scopus 로고    scopus 로고
    • Fujimura, T.; Nakashima, H.; Sakagami, H.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2002, 43, 97. See also refs 15c, d, e.
    • (d) Fujimura, T.; Nakashima, H.; Sakagami, H.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2002, 43, 97. See also refs 15c, d, e.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.