Nickel-catalyzed organozinc-promoted carbocyclizations of electron-deficient alkenes with tethered unsaturation

Journal of the American Chemical Society

Volumn 119, Issue 21, 1997, Pages 4911-4920

  Montgomery, John ^a   Oblinger, Eric ^a   Savchenko, Alexey V ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; NICKEL; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CYCLIZATION; ELECTRON TRANSPORT; OXIDATION; STRUCTURE ACTIVITY RELATION;

EID: 0030908437     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9702125     Document Type: Article

References (80)

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75. The author has deposited atomic coordinates for 24 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
76. Diene 27 was prepared by Wittig olefination of (E)-5,7-octadienal. (E)-5,7-Octadienal was prepared from 2,3-dihydropyran by α-alkylation (a), ring-opening (b), and Taber modified swern oxidation (c). (a) Margot, C.; Rizzolio, M.; Schlosser, M. Tetrahedron 1990, 46, 2411. (b) Viola, A.; Collins, J. J.; Fillip, N.; Locke, J. S. J. Org. Chem. 1993, 58, 5067. (c) Taber, D. F., Amedio Jr., J. C.; Jung, K-Y. J. Org. Chem. 1987, 52, 5621.
77. Diene 27 was prepared by Wittig olefination of (E)-5,7-octadienal. (E)-5,7-Octadienal was prepared from 2,3-dihydropyran by α-alkylation (a), ring-opening (b), and Taber modified swern oxidation (c). (a) Margot, C.; Rizzolio, M.; Schlosser, M. Tetrahedron 1990, 46, 2411. (b) Viola, A.; Collins, J. J.; Fillip, N.; Locke, J. S. J. Org. Chem. 1993, 58, 5067. (c) Taber, D. F., Amedio Jr., J. C.; Jung, K-Y. J. Org. Chem. 1987, 52, 5621.
78. Diene 27 was prepared by Wittig olefination of (E)-5,7-octadienal. (E)-5,7-Octadienal was prepared from 2,3-dihydropyran by α-alkylation (a), ring-opening (b), and Taber modified swern oxidation (c). (a) Margot, C.; Rizzolio, M.; Schlosser, M. Tetrahedron 1990, 46, 2411. (b) Viola, A.; Collins, J. J.; Fillip, N.; Locke, J. S. J. Org. Chem. 1993, 58, 5067. (c) Taber, D. F., Amedio Jr., J. C.; Jung, K-Y. J. Org. Chem. 1987, 52, 5621.
79. 2-mediated ring opening and acylation, ester hydrolysis, and Taber-modified Swern oxidation (see ref 38c). (a) Synerholm, M. E. Organic Syntheses; Wiley: New York, 1955; Collect. Vol III, p 187. (b) Earl, H. A., Sterling, J. M. J. Chem. Soc., Perkin Trans. II 1987, 1273.
80. 2-mediated ring opening and acylation, ester hydrolysis, and Taber-modified Swern oxidation (see ref 38c). (a) Synerholm, M. E. Organic Syntheses; Wiley: New York, 1955; Collect. Vol III, p 187. (b) Earl, H. A., Sterling, J. M. J. Chem. Soc., Perkin Trans. II 1987, 1273.