Density functional studies on copper-catalyzed asymmetric cyclopropanation of diazoacetate with alkene

Journal of Molecular Structure: THEOCHEM

Volumn 711, Issue 1-3, 2004, Pages 193-199

  Meng, Qingxi ^a   Li, Ming ^a   Tang, Dianyong ^a   Shen, Wei ^a   Zhang, Jinsheng ^a  

^a SOUTHWEST UNIVERSITY   (China)

Author keywords

Asymmetric cyclopropanation; Asymmtric catalysis; Chiral bisoxazoline copper(I) catalyst; DFT; Mechanism for reaction

Indexed keywords

ACETIC ACID DERIVATIVE; ALKANE; AZO COMPOUND; CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANE; ALKENE; COPPER; DIAZOACETATE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CONFORMATIONAL TRANSITION; CYCLOPROPANATION; DENSITY FUNCTIONAL THEORY; REACTION OPTIMIZATION; CHEMICAL ANALYSIS; CHIRALITY; EXPERIMENT; PREDICTION; THEORETICAL STUDY;

EID: 13844276012     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2004.06.050     Document Type: Article

References (37)

1. H.W. Liu, and C.T. Walsh Biochemistry of cyclopropyl group Z. Rappoport The Chemistry of the Cyclopropyl Group 1987 Wiley New York 959 1025
2. J. Salaun Top. Curr. Chem. 207 2000 1
3. A. de Meijere 4th ed. Houben-Weyl vol. E17a/b 1997 Thieme Stuttgart 1997
4. M.P. Doyle Chem. Rev. 86 1986 919
5. M. Lautens, W. Klute, and W. Tam Chem. Rev. 36 1996 49
6. P.C. Casey, S.W. Polichnwsky, A.J. Shusterman, and C.R. Jones J. Am. Chem. Soc. 101 1979 7282
7. M.P. Doyle, R.L. Dorow, W.E. Buhro, J.H. Griffin, W.H. Tamblyn, and M.L. Trudell Organometallics 3 1984 44
8. M.P. Doyle, J.H. Griffin, V. Bagheri, and R.L. Dorow Organometallics 3 1984 53
9. M.P. Doyle, L.C. Wang, and R.L. Loh Tetrahedron Lett. 25 1984 4087
10. H.M.R. Hoffmann, A.R. Otte, A. Wilde, S. Menzer, and D. Williams J. Angew. Chem. Ed. Engl. 34 1995 101
11. S.E. Denmark, R.A. Stavenger, A.M. Faucher, and J.P. Edwards J. Org. Chem. 62 1997 3375
12. E. Nakamura, A. Hirai, and M. Nakamura J. Am. Chem. Sco. 120 1998 5844
13. A. Hirai, E. Nakamura, and M. Nakamura Chem. Lett. 1998 927
14. K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, and T. Katsuki Chem. Eur. J. 7 2001 3776
15. B.F. Straub, and P. Hofmann Angew. Chem. Int. Ed. Engl. 40 2001 1288
16. S. Bachmann, M. Furler, and A. Mezzetti Organometallics 20 2001 2108
17. F. Bernardi, A. Bottoni, and G.P. Miscione Organometallics 20 2001 2751
18. T. Ikeno, I. Iwakura, and T. Yamada J. Am. Chem. Soc. 124 2002 15152
19. S. Masammune Tetrahedron. Lett. 31 1990 6005
20. V.K. Singh, A. DattaGupta, and G. Sekar Synthesis 1997 137
21. O.G.M. Meyer, R. Frohlich, and G. Haufe Synthesis 2000 1479
22. A.D. Becke J. Chem. Phys. 98 1993 5648
23. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1998 785
24. B. Miehlich, A. Savin, H. Stoll, and H. Preuss Chem. Phys. Lett. 157 1989 200
25. E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold, NBO Version 3.1.
26. J.E. Carpenter, and F. Weinhold J. Mol. Struct. (Theochem) 169 1988 41
27. J.E. Carpenter, PhD thesis, University of Wisconsin, Madison, WI, 1987.
28. J.P. Foster, and F. Weinhold J. Am. Chem. Soc. 102 1980 7211
29. A.E. Reed, and F. Weinhold J. Chem. Phys. 78 1983 4066
30. A.E. Reed, and F. Weinhold J. Chem. Phys. 1983 1736
31. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735
32. A.E. Reed, L.A. Curtiss, and F. Weinhold Chem. Rev. 88 1988 899
33. F. Weinhold, and J.E. Carpenter Plenum 1988 227
34. R.F.W. Bader Atoms in Molecules - A Quantum Theory 1990 Oxford University Press Oxford
35. R.F.W. Bader, P.L.A. Popelier, and T.A. Keith Theoretical definition of a functional group and the molecular orbital paradigm Angew. Chem. Int. Ed. Engl. 33 1994 620
36. F. Biegler-König, J. Schönbohm, R. Derdau, D. Bayles, R.F.W. Bader, AIM, Version 1, 2000.
37. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, Jr., K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh PA, 2003.