Mechanisms of the α,α-diphenylprolinol trimethylsilyl ether-catalyzed enantioselective aza-Michael reaction

Tetrahedron

Volumn 66, Issue 42, 2010, Pages 8267-8272

  Wong, Chiong Teck ^a  

^a INSTITUTE OF HIGH PERFORMANCE COMPUTING   (Singapore)

Author keywords

Ab initio calculation; Enantioselectivity; Iminol intermediate; Michael addition; Reaction mechanism

Indexed keywords

BIPHENYL DERIVATIVE; CARBON; NITROGEN; PROLINE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MICHAEL ADDITION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 77957190435     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.08.042     Document Type: Article

References (15)

1. D. Enders, C. Wang, and J.X. Liebich Chem. - Eur. J. 15 2009 11058
2. J. Vesely, I. Ibrahem, R. Rios, G.-L. Zhao, Y. Xu, and A. Córdova Tetrahedron Lett. 48 2007 2193
3. I. Ibrahem, R. Rios, J. Vesely, G.-L. Zhao, and A. Córdova Chem. Commun. 2007 849
4. H. Sundén, R. Rios, I. Ibrahem, G.-L. Zhao, L. Eriksson, and A. Córdova Adv. Synth. Catal. 349 2007 827
5. C.T. Wong Tetrahedron 65 2009 7491
6. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785
7. A.D. Becke J. Chem. Phys. 98 1993 5648
8. E. Cances, B. Mennucci, and J. Tomasi J. Chem. Phys. 107 1997 3032
9. B. Mennucci, and J. Tomasi J. Chem. Phys. 106 1997 5151
10. B. Mennucci, E. Cances, and J. Tomasi J. Phys. Chem. B 101 1997 10506
11. M. Cossi, V. Barone, B. Mennucci, and J. Tomasi Chem. Phys. Lett. 286 1998 253
12. J. Tomasi, B. Mennucci, and E. Cances J. Mol. Struct. (Theochem) 464 1999 211
13. M. Cossi, G. Scalmani, N. Rega, and V. Barone J. Chem. Phys. 117 2002 43
14. M.W. Wong Chem. Phys. Lett. 256 1996 391
15. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, 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, and J.A. Pople Gaussian 03, Revision C.01 2004 Gaussian Wallingford, CT