The Catalytic Asymmetric Addition of Diethylzine to N-(Diphenylphosphinoyl) Imines Catalyzed by Cu(OTf)2-Chiral N-(Binaphthyl-2-yl) thiophosphoramide Ligands

Advanced Synthesis and Catalysis

Volumn 345, Issue 8, 2003, Pages 971-973

  Shi, Min ^a   Wang, Chun Jiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric addition; Asymmetric catalysis; Chiral N (thiophosphoryl) 1,1 binaphthyl 2,2 diamine; Copper(II) triflate; Diethylzinc; Imines; N ligands; N (arylmethylene) P,P diphenylphosphinic amides

Indexed keywords

COPPER DERIVATIVE; DIETHYLCHLOROTHIOPHOSPHATE; DIETHYLZINC; IMINE; LIGAND; N (BINAPHTHYL 2 YL)THIOPHOSPHORAMIDE; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHOROTHIOIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY;

EID: 0242439336     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303041     Document Type: Article

References (27)

1. a) H.-J. Federsel, A. N. Collins, G. N. Sheldrake, J. Crosby, Chirality in Industry II, John Wiley & Sons, Chichester, 1997; pp. 225-244; for a review on catalytic asymmetric addition to imines, see:
2. b) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094.
3. a) S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, J. Am. Chem. Soc. 1994, 116, 8797-8798;
4. b) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878;
5. c) K. Tomioka, I. Inoue, M. Shindo, K Koga, Tetrahedron Lett. 1991, 32, 3095-3098.
6. H. Fujihara, K. Nagai, K. Tomika, J. Am. Chem. Soc. 2000, 122, 12055-12056.
7. a) J. R. Porter, J. F. Traverse, A. H. Hoveyda, M. L. Snapper, J. Am. Chem. Soc. 2001, 123, 984-985;
8. b) during our preparation of manuscript, we found that Charette has reported the first example of catalytic enantioselective addition of dialkylzinc to N-(diphenyl-phosphinoyl) imines, see: A. A. Boezio, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 1692-1693.
9. a) H. Nakamura, K. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 4242-4243;
10. b) M. Bao, H. Nakamura, Y. Yamaoto, Tetrahedron Lett. 2000, 41, 131-134.
11. T. Hayashi, M. Ishigedani, J. Am. Chem. Soc. 2000, 122, 976-977.
12. a) K. Soai, T. Hatanaka, T. Miyazawa, J. Chem. Soc. Chem. Commun. 1992, 1097-1098;
13. b) P. G. Andersson, D. Guijarro, D. Tanner, J. Org. Chem. 1997, 62, 7364-7375;
14. c) P. Brandt, C. Hedberg, K. Lawonn, P. Pinho, P. G. Andersson, Chem. Eur. J. 1999, 5, 1692-1699;
15. d) C. Jimeno, K. S. Reddy, L. Sola, A. Moyano, M. A. Pericas, A. Riera, Org. Lett. 2000, 2, 3157-3159;
16. e) X. M. Zhang, L. Z. Gong, A. Q. Mi, X. Cui, Y. Z. Jiang, M. C. K. Choi, A. S. C. Chan, Tetrahedron Lett. 2001, 42, 6369-6372,
17. f) K. J. M. Beresford, Tetrahedron Lett. 2002, 43, 7175-7177.
18. a) I. Ojima, Ed. Catalytic Asymmetric Synthesis, VCH, New York, 1993;
19. b) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Eds. Comprehensive Asymmetric Catalysis. Springer-Verlag, Germany, 2001.
20. a) M. Shi, W.-S. Sui, Chiraliy, 2000, 12, 574-580;
21. b) M. Shi, W.-S. Sui, Tetrahedron:Asymmetry 2000, 11, 773-779;
22. c) M. Shi, W.-S. Sui, Tetrahedron Asymmetry 2000, 11, 835-841;
23. d) M. Shi, W.-S. Sui, Tetrahedron Asymmetry 1999, 10, 3319-3325.
24. S. Miyano, M. Nawa, A. Mori, H. Hashimoto, Bull. Chem. Soc. Jpn. 1984, 57, 2171-2176.
25. R. Ramage, D. Hopton, M. J. Parrot, G. W. Kenner, G. A. More, J. Chem. Soc. Perkin Trans. 1 1984, 1357-1370.
26. For selected X-ray structures of Cu complexes coordinated by S,N ligands, see: a) D. M. Koten, D. M. Grove, W. J. Smeets, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1992, 114, 3400-3410; b) G. R. Brubaker, J. N. Brown, M. K. Yoo, T. M. Kutchan, E. A. Mottel, Inorg. Chem. 1979, 18, 299-302.
27. For selected X-ray structures of Cu complexes coordinated by S,N ligands, see: a) D. M. Koten, D. M. Grove, W. J. Smeets, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1992, 114, 3400-3410; b) G. R. Brubaker, J. N. Brown, M. K. Yoo, T. M. Kutchan, E. A. Mottel, Inorg. Chem. 1979, 18, 299-302.