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Volumn 121, Issue 47, 1999, Pages 11012-11013

Transfer of chirality in radical cyclizations. Cyclization of o- haloacrylanilides to oxindoles with transfer of axial chirality to a newly formed stereocenter [6]

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE;

EID: 0033486022     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993329x     Document Type: Letter
Times cited : (122)

References (33)
  • 6
    • 0025284005 scopus 로고
    • Chemoselective reactions are also possible. For example, radical reactions are often faster than amide bond rotations, so products depend on rotamer populations of the radical precursor. (a) Snieckus, V.; Cuevas, J. C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896. (b) Musa, O. M.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1999, 64, 1022.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 896
    • Snieckus, V.1    Cuevas, J.C.2    Sloan, C.P.3    Liu, H.4    Curran, D.P.5
  • 7
    • 0033524884 scopus 로고    scopus 로고
    • Chemoselective reactions are also possible. For example, radical reactions are often faster than amide bond rotations, so products depend on rotamer populations of the radical precursor. (a) Snieckus, V.; Cuevas, J. C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896. (b) Musa, O. M.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1999, 64, 1022.
    • (1999) J. Org. Chem. , vol.64 , pp. 1022
    • Musa, O.M.1    Horner, J.H.2    Newcomb, M.3
  • 24
    • 84920351146 scopus 로고    scopus 로고
    • Unpublished results. University of Pittsburgh. A full paper describing these results is planned
    • Chen, C. H-T; Geib, S. Unpublished results. University of Pittsburgh. A full paper describing these results is planned.
    • Chen, C.H.-T.1    Geib, S.2
  • 29
    • 37049071273 scopus 로고
    • Leading references: (a) Beckwith, A. L. J.; Storey, J. M. D. J. Chem. Soc. Chem. Commun. 1995, 977. (b) Jones, K.; Storey, J. M. D. Tetrahedron Lett. 1993, 34, 7797. (c) Bowman, W. R.; Heaney, H.; Jordan, B. M. Tetrahedron Lett. 1988, 29, 6657.
    • (1995) J. Chem. Soc. Chem. Commun. , pp. 977
    • Beckwith, A.L.J.1    Storey, J.M.D.2
  • 30
    • 0027384279 scopus 로고
    • Leading references: (a) Beckwith, A. L. J.; Storey, J. M. D. J. Chem. Soc. Chem. Commun. 1995, 977. (b) Jones, K.; Storey, J. M. D. Tetrahedron Lett. 1993, 34, 7797. (c) Bowman, W. R.; Heaney, H.; Jordan, B. M. Tetrahedron Lett. 1988, 29, 6657.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7797
    • Jones, K.1    Storey, J.M.D.2
  • 31
    • 0000854312 scopus 로고
    • Leading references: (a) Beckwith, A. L. J.; Storey, J. M. D. J. Chem. Soc. Chem. Commun. 1995, 977. (b) Jones, K.; Storey, J. M. D. Tetrahedron Lett. 1993, 34, 7797. (c) Bowman, W. R.; Heaney, H.; Jordan, B. M. Tetrahedron Lett. 1988, 29, 6657.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 6657
    • Bowman, W.R.1    Heaney, H.2    Jordan, B.M.3
  • 33
    • 0032496939 scopus 로고    scopus 로고
    • For example, Overman and co-workers have reported catalytic asymmetric Heck reactions of related o-iodoanilides lacking the second ortho substituent. One possible origin (among several others) for the stereoselection in these reactions is that stereoselective insertion of the chiral catalyst into one of the (equilibrating) enantiomeric iodides (dynamic kinetic resolution) is followed by an insertion into the nearby C=C bond that is faster than N-Ar bond rotation. See: Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6488
    • Ashimori, A.1    Bachand, B.2    Calter, M.A.3    Govek, S.P.4    Overman, L.E.5    Poon, D.J.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.