BINOL-based azacrown ether catalyzed enantioselective Michael addition: Asymmetric synthesis of α-aminophosphonates

Tetrahedron Asymmetry

Volumn 22, Issue 4, 2011, Pages 480-486

  Pham, Truong Son ^a   Czirok, János B ^a   Balázs, László ^b   Pál, Krisztina ^c   Kubinyi, Miklós ^c   Bitter, István ^a,c   Jászay, Zsuzsa ^d  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b Chinoin Pharmaceutical and Chemical Works Ltd   (Hungary)

^c CHEMICAL RESEARCH CENTER   (Hungary)

^d INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; 4 (BENZHYDRYLIDENE AMINO) 4(DIETHOXY PHOSPHORYL) 2 METHYL BUTYRIC ACID TERT BUTYL ESTER; 4 (BENZHYDRYLIDENE AMINO) 4(DIETHOXY PHOSPHORYL) BUTYRIC ACID TERT BUTYL ESTER; ACRYLONITRILE; ALPHA AMINOPHOSPHONATE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; [(BENZHYDRYLIDENE AMINO) 3 CYANO PROPYL] PHOSPHONIC ACID DIETHYL ESTER; [(BENZHYDRYLIDENE AMINO) CYANO 3 METHYL PROPYL] PHOSPHONIC ACID DIETHYL ESTER; [1 (BENZHYDRYLIDENE AMINO) 3 CYANO 2 PHENYL PROPYL] PHOSPHONIC ACID DIETHYL ESTER; [1 (BENZHYDRYLIDENE AMINO) 3 DIMETHYLCARBAMOYL PROPYL] PHOSPHONIC ACID DIETHYL ESTER;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MICHAEL ADDITION; PRIORITY JOURNAL;

EID: 84962427514     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.02.002     Document Type: Article

References (47)

1. For reviews see: J.M. Brunel Chem. Rev. 105 2005 857 897 Update 1: Chem. Rev. 2007, 107, PR1-PR45
2. Y. Chen, S. Yakta, and A.K. Yudin Chem. Rev. 103 2003 3155 3212
3. P. Kočovsky, Š. Viskočil, and M. Smrčina Chem. Rev. 103 2003 3213 3246
4. R.M. Izatt, C.Y. Zhu, P. Huszthy, and J.S. Bradshaw Enantiomeric Recognition in Macrocycle-Primary Ammonium Cation System S.R. Cooper, Crown Compounds: Toward Future Applications 1992 VCH New York Chapter 12
5. E.B. Kyba, K. Koga, L.R. Sousa, M.G. Siegel, and D.J. Cram J. Am. Chem. Soc. 95 1973 2692 2693
6. Y. Kubo Synlett 1999 161 174
7. I. Bitter, É. Kszegi, A. Grün, P. Bakó, K. Pál, A. Grofcsik, M. Kubinyi, B. Balázs, and G. Tóth Tetrahedron: Asymmetry 14 2003 1025 1035
8. X.X. Zhang, J.S. Bradshaw, and R.M. Izatt Chem. Rev. 97 1997 3313 3362
9. K. Tsubaki, H. Tanaka, T. Kinoshita, and K. Fuji Tetrahedron 58 2002 1679 1684
10. K. Tsubaki, H. Tanaka, H. Morikawa, and K. Fuji Tetrahedron 59 2003 3195 3199
11. J.P. Mazaleyrat, K. Wright, M.-V. Azzini, A. Gaucher, and M. Wakselman Tetrahedron Lett. 44 2003 1741 1745
12. A. Grün, É. Kszegi, and I. Bitter Tetrahedron 60 2004 5041 5048
13. K.S. Kim, E.J. Jun, S.K. Kim, H.J. Choi, J. Joo, C.-H. Lee, M.H. Hyun, and J. Yoon Tetrahedron Lett. 48 2007 2481 2484
14. É. Kszegi, A. Grün, and I. Bitter Supramol. Chem. 18 2006 67 76
15. P. Bakó, Á. Szöllsy, P. Bombicz, and L. Tke Synlett 1997 291 292
16. T. Bakó, P. Bakó, Á. Szöllsy, M. Czugler, Gy. Keglevich, and L. Tke Tetrahedron: Asymmetry 13 2002 203 209
17. T. Bakó, P. Bakó, Gy. Keglevich, N. Báthori, M. Czugler, J. Tatai, T. Novák, Gy. Parlagh, and L. Tke Tetrahedron: Asymmetry 14 2003 1917 1923
18. P. Kafarski, and B. Lejczak Phosphorus Sulfur Silicon Relat. Elem. 63 1991 193 215
19. J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassal, S.W. Holmes, R.W. Lambert, L.J. Nisbert, and P.S. Ringrose Nature 272 1978 56 58
20. F.R. Atherton, C.H. Hassall, and R.W. Lambert J. Med. Chem. 29 1986 29 40
21. M.C. Allen, W. Fuhrer, B. Tuck, R. Wade, and J.M. Wood J. Med. Chem. 32 1989 1652 1661
22. R. Rozenfeld, X. Iturrioz, M. Okada, B. Maigret, and C. Llorens-Cortes Biochemistry 42 2003 14785 14793
23. S.S. Abdel-Meguid, B. Zhao, K.H.M. Murthy, E. Winborne, J.K. Choi, R.L. DesJarlais, M.D. Minnich, J.S. Culp, and C. Debouck Biochemistry 32 1993 7972 7980
24. A.B. Smith III, C.M. Taylor, S.R. Benkovic, and R. Hirschman Tetrahedron Lett. 35 1994 6853
25. F. Tanaka, K. Kinoshita, R. Tanimura, and I. Fuji J. Am. Chem. Soc. 118 1996 2332 2339
26. For P-C bond formation see: H. Sasai, S. Arai, Y. Tahara, and M. Shibasaki J. Org. Chem. 60 1995 6656 6657
27. T. Akiyama, H. Morita, J. Itoh, and K. Fuchibe Org. Lett. 7 2005 2583 2585
28. G.D. Joly, and E.N. Jacobsen J. Am. Chem. Soc. 126 2004 4102 4103
29. D. Pettersen, M. Marcolini, L. Bernardi, F. Fini, R.P. Herrera, V. Sgarzani, and A. Ricci J. Org. Chem. 71 2006 6269 6272
30. For C-C bond formation see: Zs.M. Jászay, G. Németh, S.P. Truong, I. Petneházy, A. Grn, and L. Tke Tetrahedron: Asymmetry 16 2005 3837 3840
31. Zs.M. Jászay, S.P. Truong, G. Németh, P. Bakó, I. Petneházy, and L. Tke Synlett 2009 1429 1432
32. For P-C bond formation see: A.B. Smith III, K.M. Yager, and C.M. Taylor J. Am. Chem. Soc. 117 1995 10879 10888
33. M. Mikolajczyk, P. Lyzwa, and J. Drabowicz Tetrahedron: Asymmetry 8 1997 3991 3994
34. I.M. Lefebvre, and A.S. Evans Jr. J. Org. Chem. 62 1997 7532 7533
35. F.A. Davis, S. Lee, H. Yan, and D.D. Titus Org. Lett. 3 2001 1757 1760
36. For C-C bond formation see: U. Schöllkopf, and R. Schütze Liebigs Ann. Chem. 1987 45 49
37. U. Groth, L. Richter, and U. Schöllkopf Liebigs Ann. Chem. 1992 903 909
38. F. Ouazzani, M.L. Roumestant, and P. Viallefont Tetrahedron: Asymmetry 2 1991 913 917
39. J. Oleksyszyn V.P. Kukhar, H.R. Hudson, Aminophosphonic and Aminophosphinic Acids 2000 John Wiley and Sons Chichester 537 558 Chapter15
40. M. Ordonez, H. Rojas-Cabrera, and C. Cativiela Tetrahedron 65 2009 17 49
41. Marvin 5.2.5.1., 2009, ChemAxon. http://www.chemaxon.com.
42. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B37 1988 785
43. A.D. Becke J. Chem. Phys. 98 1993 5648
44. P.C. Hariharan, and J.A. Pople Theor. Chim. Acta 28 1973 213
45. 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, V. Bakken, 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 B.01 2003 Gaussian Pittsburg, PA
46. D.M. McCann, and P.J. Stephens J. Org. Chem. 71 2006 6074
47. S. Miertus, E. Scrocco, and J. Tomasi Chem. Phys. 55 1981 117