Catalytic enantioselective hydrophosphonylation of ketimines using cinchona alkaloids

Journal of the American Chemical Society

Volumn 131, Issue 51, 2009, Pages 18240-18241

  Nakamura, Shuichi ^a   Hayashi, Masashi ^a   Hiramatsu, Yuichi ^a   Shibata, Norio ^a   Funahashi, Yasuhiro ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOPHOSPHONATES; CATALYST LOADINGS; CHEMICAL EQUATIONS; CINCHONA ALKALOID; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; HYDROPHOSPHONYLATION; KETIMINES; ORGANOCATALYTIC;

CHEMICAL REACTIONS; ENANTIOSELECTIVITY; SODIUM;

ELECTRON TRANSITIONS;

ALKALOID DERIVATIVE; CINCHONA ALKALOID; HYDROQUININE; KETONE DERIVATIVE; QUININE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CRYSTALLIZATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOSPHONYLATION; REACTION ANALYSIS;

CATALYSIS; CINCHONA ALKALOIDS; IMINES; NITRILES; PHOSPHONIC ACIDS; STEREOISOMERISM;

EID: 73249115987     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja908940e     Document Type: Article

References (18)

1. For reviews of the biological activity of α-amino phosphonic acids, see: (a) Hiratake, J.; Oda, J. Biosci., Biotechnol., Biochem. 1997, 61, 211.
2. (b) Aminophosphonic and Aminophosphinic Acids; Kukhar, V. P., Hudson, H. R., Eds.; John Wiley & Sons: New York, 2000.
3. (a) Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassal, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Nature 1978, 272, 56.
4. (b) Atherton, F. R.; Hassall, C. H.; Lambert, R. W. J. Med. Chem. 1986, 29, 29.
5. (a) Stowasser, B.; Budt, K.-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625.
6. (b) Alonso, E.; Solis, A.; del Pozo, C. Synlett 2000, 698.
7. For selected examples, see: (a) Hirschmann, R.; Smith, A. B., III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Benkovic, S. J. Science 1994, 265, 234.
8. (b) Smith, W. W.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4622, and references therein.
9. For reviews of enantioselective hydrophosphonylation of imines, see: (a) Merino, P.; Marqués-López, E.; Herrera, R. P. Adv. Synth. Catal. 2008, 350, 1195.
10. (b) Ordóñez, M.; Rojas-Cabrera, H.; Cativiela, C. Tetrahedron 2009, 65, 17, and references therein.
11. For reviews of enantioselective reactions of ketimines, see: (a) Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853.
12. (b) Bella, M.; Gasperi, T. Synthesis 2009, 1583, and references therein.
13. For diastereoselective addition of lithiated phosphonates to chiral N-sulfinylketimines, see: (a) Davis, F. A.; Lee, S.; Yan, H.; Titus, D. D. Org. Lett. 2001, 3, 1757.
14. (b) Chen, Q.; Yuan, C. Synthesis 2007, 3779.
15. Nakamura, S.; Nakashima, H.; Yamamura, A.; Shibata, N.; Toru, T. Adv. Synth. Catal. 2008, 350, 1209.
16. We also reported the enantioselective reaction of N-sulfonylimines. See: (a) Nakamura, S.; Nakashima, H.; Sugimoto, H.; Sano, H.; Hattori, M.; Shibata, N.; Toru, T. Chem.-Eur. J. 2008, 14, 2145.
17. (b) Nakamura, S.; Sakurai, Y.; Nakashima, H.; Shibata, N.; Toru, T. Synlett 2009, 1639.
18. 3.