메뉴 건너뛰기




Volumn 38, Issue 16, 1999, Pages 2384-2386

Samarium-mediated β-elimination in dihalo alcohols: Diastereoselective synthesis of (Z)-vinyl halides

Author keywords

Alkenes; Eliminations; Samarium; Vinyl halides

Indexed keywords

1 BROMO 3 CHLORO 5,5 DIMETHYLHYDANTOIN; ALKENE; HALIDE; SAMARIUM;

EID: 0033549735     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2384::AID-ANIE2384>3.0.CO;2-3     Document Type: Article
Times cited : (47)

References (38)
  • 3
    • 0000871832 scopus 로고
    • (Eds.: B. M. Trost, I. Flemming, E. Winterfeldt), Pergamon, Oxford
    • a) A. Krebs, J. Swienty-Busch, Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Flemming, E. Winterfeldt), Pergamon, Oxford, 1991, pp. 949-974;
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 949-974
    • Krebs, A.1    Swienty-Busch, J.2
  • 4
    • 0000352213 scopus 로고
    • (Eds.: B. M. Trost, I. Flemming, E. Winterfeldt), Pergamon, Oxford
    • b) P. Kocienski, Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Flemming, E. Winterfeldt), Pergamon, Oxford, 1991, pp. 975-1010.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 975-1010
    • Kocienski, P.1
  • 8
    • 0001143131 scopus 로고
    • For examples of the preparation of vinyl halides, see: a) H. C. Brown, C. Subrahmanyam, T. Hamaoka, N. Ravindran, D. H. Bowman, S. Misumi, M. K. Unni, V. Somayaji, N. G. Bhat, J. Org. Chem. 1989, 54, 6068-6075; b) H. C. Brown, T. Hamaoka, N. Ravindran, C. Subrahmanyam, V. Somayaji, N. G. Bhat, J. Org. Chem. 1989, 54, 6075; c) G. Stork, K. Zhao, Tetrahedron Lett. 1989, 30, 2173-2174.
    • (1989) J. Org. Chem. , vol.54 , pp. 6075
    • Brown, H.C.1    Hamaoka, T.2    Ravindran, N.3    Subrahmanyam, C.4    Somayaji, V.5    Bhat, N.G.6
  • 9
    • 0001647908 scopus 로고
    • For examples of the preparation of vinyl halides, see: a) H. C. Brown, C. Subrahmanyam, T. Hamaoka, N. Ravindran, D. H. Bowman, S. Misumi, M. K. Unni, V. Somayaji, N. G. Bhat, J. Org. Chem. 1989, 54, 6068-6075; b) H. C. Brown, T. Hamaoka, N. Ravindran, C. Subrahmanyam, V. Somayaji, N. G. Bhat, J. Org. Chem. 1989, 54, 6075; c) G. Stork, K. Zhao, Tetrahedron Lett. 1989, 30, 2173-2174.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2173-2174
    • Stork, G.1    Zhao, K.2
  • 10
    • 2442729636 scopus 로고
    • (Eds.: B. M. Trost, I. Flemming, M. F. Semmelhock), Pergamon, Oxford
    • a) R. F. Heck, Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Flemming, M. F. Semmelhock), Pergamon, Oxford, 1991, pp. 851-856;
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 851-856
    • Heck, R.F.1
  • 15
    • 0003184360 scopus 로고    scopus 로고
    • e) K. C. Nicolau, Y. He, F. Roschangar, N. P. King, D. Vourloumis, T. Li, Angew. Chem. 1998, 110, 89-92; Angew. Chem. Int. Ed. 1998, 37, 84-87.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 84-87
  • 28
    • 2442741550 scopus 로고    scopus 로고
    • [11]
    • [11]
  • 29
    • 2442737037 scopus 로고    scopus 로고
    • 1H NMR coupling constant of the major and minor diastereoisomers
    • 1H NMR coupling constant of the major and minor diastereoisomers.
  • 30
    • 2442757214 scopus 로고    scopus 로고
    • 13C NMR spectroscopy and was similar to that of the purified products
    • 13C NMR spectroscopy and was similar to that of the purified products.
  • 31
    • 0001619131 scopus 로고    scopus 로고
    • 2-promoted reactions, apparently with very different mechanisms. To date, no explanation has been suggested. See a) G. A. Molander, C. R. Harris, J. Org. Chem. 1998, 63, 812-816; b) J. M. Aurrecoechea, B. López, Tetrahedron Lett. 1998, 39, 2857, and references therein; see also ref. [9a].
    • (1998) J. Org. Chem. , vol.63 , pp. 812-816
    • Molander, G.A.1    Harris, C.R.2
  • 32
    • 0032580421 scopus 로고    scopus 로고
    • and references therein; see also ref. [9a]
    • 2-promoted reactions, apparently with very different mechanisms. To date, no explanation has been suggested. See a) G. A. Molander, C. R. Harris, J. Org. Chem. 1998, 63, 812-816; b) J. M. Aurrecoechea, B. López, Tetrahedron Lett. 1998, 39, 2857, and references therein; see also ref. [9a].
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2857
    • Aurrecoechea, J.M.1    López, B.2
  • 35
    • 0001272931 scopus 로고    scopus 로고
    • 2: a) G. A. Molander, J. B. Etter, P. W. Zinke, J. Am. Chem. Soc. 1987, 109, 453-463; b) D. Urban, T. Skrydstrup, J.-M. Beau, J. Org. Chem. 1998, 63, 2507-2516.
    • (1998) J. Org. Chem. , vol.63 , pp. 2507-2516
    • Urban, D.1    Skrydstrup, T.2    Beau, J.-M.3
  • 38
    • 0030933939 scopus 로고    scopus 로고
    • b) S. Matsubara, M. Yoshioka, K. Utimoto, Angew. Chem. 1997, 109, 631-633; Angew. Chem. Int. Ed. Engl. 1997, 36, 617-618.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 617-618


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.