Stereoselective formation and rearrangement of morpholinium ylides derived from copper carbenoids

Tetrahedron Asymmetry

Volumn 14, Issue 7, 2003, Pages 917-920

  Glaeske, Kevin W ^a   Naidu, B N ^a   West, F G ^a,b  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; AMMONIUM DERIVATIVE; CARBENOID; COPPER DERIVATIVE; KETONE DERIVATIVE; MORPHOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; CONFORMATIONAL TRANSITION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0037418811     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00095-8     Document Type: Article

References (32)

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11. Reviews of asymmetric approaches to unnatural amino acid derivatives: (a) Willams, R. M. Synthesis of Optically Active α-Amino Acids, Pergamon: Oxford, 1989; (b) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (c) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599; (d) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732.
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13. (a) Glaeske, K. W.; Arif, A. M.; West, F. G. Org. Lett. 1999, 1, 31-33;
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24. 2.
25. The congested steric environment of dibenzylamines has been noted previously: (a) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143; (b) Review: Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162.
26. The congested steric environment of dibenzylamines has been noted previously: (a) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143; (b) Review: Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162.
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29. 3: C, 70.31; H, 7.01; N, 5.12. Found: C, 70.07; H, 6.95; N, 4.99%.
30. Crystallographic data (excluding structure factors) for compound 9a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 200163. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
31. Vedejs, E.; Arco, M. J.; Powell, D. W.; Renga, J. M.; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837. See also Refs 5a,c and 6a-f.
32. The radical-pair mechanism for [1,2]-shifts of ammonium ylides is well-established. See: Ollis, W. D.; Rey, M.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1983, 1009-1027.