A DFT study of the asymmetric (S)-5-(pyrrolidin-2-yl)-1H-tetrazole catalyzed Michael addition of carbonyl compounds to nitroalkenes

Tetrahedron Asymmetry

Volumn 18, Issue 2, 2007, Pages 157-164

  Arnó, Manuel ^a   Zaragozá, Ramón J ^a   Domingo, Luis R ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

5 (PYRROLIDIN 2 YL) 1H TETRAZOLE; ACID; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; HYDROGEN; NITRO DERIVATIVE; OXYGEN; PYRROLIDINE DERIVATIVE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; MICHAEL ADDITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 33847114330     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.01.011     Document Type: Article

References (38)

1. Perlmutter P. Conjugate Addition Reactions in Organic Synthesis (1992), Pergamon Press, Oxford
2. Jacobsen E.N., Pfaltz A., and Yamamoto H. Comprehensive Asymmetric Catalysis (1999), Springer, New York
3. Krause N., and Hoffmann-Roder A. Synthesis (2001) 171
4. Hajos Z.G., and Parrish D.R. J. Org. Chem. 39 (1974) 1615
5. List B., Pojarliev P., and Castello C. Org. Lett. 3 (2001) 537
6. Szollosi G., Lonfon G., Balaspiri L., Somlai C., and Bartok M. Chirality 15 (2003) S90
7. Northrup A.B., and MacMillan D.W.C. J. Am. Chem. Soc. 124 (2002) 6798
8. Bui T., and Barbas III C.F. Tetrahedron Lett. 41 (2000) 6951
9. Rajagopal D., Narayanan R., and Swaminathan S. Tetrahedron Lett. 42 (2001) 4887
10. Córdova A., Notz W., Zhong G., Betancort J.M., and Barbas III C.F. J. Am. Chem. Soc. 124 (2002) 1842
11. Córdova A., Watanabe S.-i., Tanaka F., Notz W., and Barbas III C.F. J. Am. Chem. Soc. 124 (2002) 1866
12. Pojarliev P., Biller W.T., Martin H.J., and List B. Synlett (2003) 1903
13. Chowdari N.S., Ramachary D.B., and Barbas III C.F. Synlett (2003) 1906
14. Notz W., Tanaka F., Watanabe S.-i., Chowdari N.S., Turner J.M., Thayumanavan R., and Barbas III C.F. J. Org. Chem. 68 (2003) 9624
15. Itoh T., Yokoya M., Miyauchi K., Nagata K., and Ohsawa A. Org. Lett. 5 (2003) 4301
16. Butler R.N. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 4 (1996), Pergamon, Oxford, UK
17. Herr R. J. Bioorg. Med. Chem. 10 (2002) 3379
18. Cobb A.J.A., Shaw D.M., Longbottom D.A., Gold J.B., and Ley S.V. Org. Biomol. Chem. 3 (2005) 84
19. Enders D., and Seki A. Synlett (2002) 26
20. Betancort J.M., Sakthivel K., Thayumanavan R., Tanaka F., and Barbas III C.F. Synthesis (2004) 1509
21. Ishii T., Fujioka S., Sekiguchi Y., and Kotsuki H. J. Am. Chem. Soc. 126 (2004) 9558
22. Arnó M., and Domingo L.R. Theor. Chem. Acc. 108 (2002) 232
23. Arnó M., Zaragozá R.J., and Domingo L.R. Tetrahedron: Asymmetry 15 (2004) 1541
24. Arnó M., Zaragozá R.J., and Domingo L.R. Tetrahedron: Asymmetry 16 (2005) 2764
25. Parr R.G., and Yang W. Density Functional Theory of Atoms and Molecules (1989), Oxford University Press, New York
26. Ziegler T. Chem. Rev. 91 (1991) 651
27. Becke A.D. J. Chem. Phys. 98 (1993) 5648
28. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
29. Hehre W.J., Radom L., Schleyer P.v.R., and Pople J.A. Ab initio Molecular Orbital Theory (1986), Wiley, New York
30. Tomasi J., and Persico M. Chem. Rev. 94 (1994) 2027
31. Simkin B.Y., and Sheikhet I. Quantum Chemical and Statistical Theory of Solutions-A Computational Approach (1995), Ellis Horwood, London
32. Cances E., Mennucci B., and Tomasi J. J. Chem. Phys. 107 (1997) 3032
33. Cossi M., Barone V., Cammi R., and Tomasi J. Chem. Phys. Lett. 255 (1996) 327
34. Barone V., Cossi M., and Tomasi J. J. Comput. Chem. 19 (1998) 404
35. Reed A.E., Weinstock R.B., and Weinhold F. J. Chem. Phys. 83 (1985) 735
36. Reed A.E., Curtiss L.A., and Weinhold F. Chem. Rev. 88 (1988) 899
37. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Wallingford, CT
38. Wiberg K.B. Tetrahedron 24 (1968) 1083