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Volumn 131, Issue 42, 2009, Pages 15492-15500

Synthesis of highly enantioenriched 3,4-dihydroquinolin-2-ones by 6-Exo-trig radical cyclizations of axially chiral α-halo-ortho-alkenyl anilides

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; ANILIDES; AXIAL CHIRALITY; CHIRALITY TRANSFER; CYCLIZATIONS; DIASTEREO-SELECTIVITY; HIGH FIDELITY; HIGH YIELD; RADICAL CYCLIZATIONS; RADICAL REACTIONS; REACTIVE SPECIES; STEREOCENTERS;

EID: 70350316746     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9066282     Document Type: Article
Times cited : (43)

References (68)
  • 1
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    • For a more complete collection of references to biologically active 3,4-dihydroquinolin-2-ones and methods of synthesis, see
    • For a more complete collection of references to biologically active 3,4-dihydroquinolin-2-ones and methods of synthesis, see: Zhou, W.; Zhang, L.; Jiao, N. Tetrahedron 2009, 65, 1982-1987.
    • (2009) Tetrahedron , vol.65 , pp. 1982-1987
    • Zhou, W.1    Zhang, L.2    Jiao, N.3
  • 20
    • 0037419167 scopus 로고    scopus 로고
    • Other radical approaches include bimolecular additions, see ref 1, and cyclizations to isocyanates, see
    • Other radical approaches include bimolecular additions, see ref 1, and cyclizations to isocyanates, see: Minin, P. L.; Walton, J. C. J. Org. Chem. 2003, 68, 2960-2963.
    • (2003) J. Org. Chem. , vol.68 , pp. 2960-2963
    • Minin, P.L.1    Walton, J.C.2
  • 22
    • 0026646629 scopus 로고
    • Related additions to aryl rings
    • (b) Clark, A. J.; Jones, K. Tetrahedron 1992, 48, 6875-6882. Related additions to aryl rings:
    • (1992) Tetrahedron , vol.48 , pp. 6875-6882
    • Clark, A.J.1    Jones, K.2
  • 28
    • 0002999412 scopus 로고
    • Allinger, N. L., Eliel, E., Wilen, S. H., Eds.; Wiley InterScience: New York
    • (a) Oki, M. In Topics in Stereochemistry; Allinger, N. L., Eliel, E., Wilen, S. H., Eds.; Wiley InterScience: New York, 1983; Vol.14, pp 1-81.
    • (1983) Topics in Stereochemistry , vol.14 , pp. 1-81
    • Oki, M.1
  • 43
  • 45
    • 0001789449 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
    • Yorimitsu, H.; Oshima, K. In Radicals in organic synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol.1, pp 11-27.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 11-27
    • Yorimitsu, H.1    Oshima, K.2
  • 49
  • 50
    • 0000782249 scopus 로고    scopus 로고
    • 1st ed.; Renard, P., Sibi, M., Eds.; Wiley-VCH: Weinheim
    • (b) Newcomb, M. In Radicals in Organic Synthesis, 1st ed.; Renard, P., Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001; Vol.1, pp 317-336.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 317-336
    • Newcomb, M.1
  • 63
    • 33845281761 scopus 로고
    • Interestingly, however, the rate of rotation about the NC(O)-CHMe(•) may be similar to or possibly even slower than the rate of radical cyclization. If that is the case, then both diastereomers of precursor must produce the same s-cis radical. For rotation rate information, see: (a)
    • Interestingly, however, the rate of rotation about the NC(O)-CHMe(•) may be similar to or possibly even slower than the rate of radical cyclization. If that is the case, then both diastereomers of precursor must produce the same s-cis radical. For rotation rate information, see: (a) Strub, W.; Roduner, E.; Fischer, H. J. Phys. Chem. 1987, 91, 4379-4383.
    • (1987) J. Phys. Chem. , vol.91 , pp. 4379-4383
    • Strub, W.1    Roduner, E.2    Fischer, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.