Highly enantioselective hydrophosphonylation of aldehydes: Base-enhanced aluminum-salalen catalysis

Angewandte Chemie - International Edition

Volumn 49, Issue 4, 2010, Pages 797-799

  Suyama, Keitaro ^a   Sakai, Yoshifumi ^a   Matsumoto, Kazuhiro ^a   Saito, Bunnai ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Aldehydes; Aluminum; Asymmetric catalysis; Hydrophosphonylation; Phosphonates

Indexed keywords

ASYMMETRIC CATALYSIS; CHEMICAL EQUATIONS; COMPLEX 1; CONJUGATED ALDEHYDES; ENANTIOSELECTIVE; ENHANCED ALUMINUM; HYDROPHOSPHONYLATION; PHOSPHONATES;

ALDEHYDES; CATALYSIS;

ALUMINUM;

ALDEHYDE; ALUMINUM; ORGANOMETALLIC COMPOUND; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; ALUMINUM; CATALYSIS; ORGANOMETALLIC COMPOUNDS; PHOSPHONIC ACIDS; STEREOISOMERISM;

EID: 74849104656     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905158     Document Type: Article

References (45)

1. a) J. Stawinski, A. Kraszewski, Acc. Chem. Res. 2002, 35, 952-960;
2. b) B. Stowasser, K.-H. Budt, L. Jian-Qi, A. Peyman, D. Ruppert, Tetrahedron Lett. 1992, 33, 6625-6628.
3. For recent reviews on asymmetric hydrophosphonylation, see: a) H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948;
4. b) P. Merino, E. Marqués-López, R. P. Herrera, Adv. Synth. Catal. 2008, 350, 1195-1208.
5. For selected examples of asymmetric hydrophosphonylation, see: a) T. Yokomatsu, T. Yamagishi, S. Shibuya, Tetrahedron: Asymmetry 1993, 4, 1779-1782;
6. b) T. Yokomatsu, T. Yamagishi, S. Shibuya, Tetrahedron: Asymmetry 1993, 4, 1783-1784;
7. c) N. P. Rath, C. D. Spilling, Tetrahedron Lett. 1994, 35, 227-230;
8. d) T. Arai, M. Bougauchi, H. Sasai, M. Shibasaki, J. Org. Chem. 1996, 67, 2926-2927;
9. e) T. Yokomatsu, T. Yamagishi, K. Matsumoto, S. Shibuya, Tetrahedron 1996, 52, 11725-11738;
10. f) H. Sasai, M. Bougauchi, T. Arai, M. Shibasaki, Tetrahedron Lett. 1997, 38, 271.7-2720;
11. g) T. Yokomatsu, T. Yamagishi, S. Shibuya, J. Chem. Soc. Perkin Trans. 1 1997, 1527-1533;
12. h) M. D. Groaning, B. J. Rowe, C. D. Spilling, Tetrahedron Lett. 1998, 39, 5485-5488;
13. i) D. M. Cermak, Y. Du, D. F. Wiemer, J. Org. Chem. 1999, 64, 388-393;
14. j) T. Yamagishi, T. Yokomatsu, K. Suemune, S. Shibuya, Tetrahedron 1999, 55, 12125-12136;
15. k) J. P. Duxbury, A. Cawley, M. Thornton-Pett, L. Wantz, J. N. D. Warne, R. Greatrex, D. Brown, T. P. Kee, Tetrahedron Lett. 1999, 40, 4403-4406;
16. l) C. V. Ward, M. Jiang, T. P. Kee, Tetrahedron Lett. 2000, 41, 6181-6184;
17. m) J. P. Duxbury, J. N. D. Warne, R. Mushtuq, C. Ward, M. Thornton-Pett, M. Jiang, R. Greatrex, T. P. Kee, Organometallics 2000, 19, 4445-4457;
18. n) D. Skropeta, R. R. Schmidt, Tetrahedron: Asymmetry 2003, 14, 265-273;
19. o) T. D. Nixon, S. Dalgarno, C. V. Ward, M. Jiang, M. C. Halcrow, C. Kilner, M. Thornton-Pett, T. P. Kee, C. R. Chim. 2004, 7, 809-821;
20. p) K. Ito, H. Tsutsumi, M. Setoyama, B. Saito, T. Katsuki, Synlett 2007, 1960-1962;
21. q) S. Gou, X. Zhou, J. Wang, X. Liu, X. Feng, Tetrahedron 2008, 64, 2864-2870;
22. r) X. Zhou, X. Liu, X. Yang, D. Shang, J. Xin, X. Feng, Angew. Chem. 2008, 120, 398-400;
23. Angew. Chem. Int. Ed. 2008, 47, 392-394;
24. s) F. Yang, D. Zhao, J. Lan, P. Xi, L. Yang, S. Xiang, J. You, Angew. Chem. 2008, 120, 5728-5731;
25. Angew. Chem. Int. Ed. 2008, 47, 5646-5649.
26. a) O. I. Kolodiazhnyi, Tetrahedron: Asymmetry 2005, 16, 3295-3350;
27. b) V. D. Pawar, S. Bettigeri, S.-S. Weng, J.-Q. Kao, C.-T. Chen, J. Am. Chem. Soc. 2006, 128, 6308-6309;
28. c) S. Samanta, C.-G. Zhao, J. Am. Chem. Soc. 2006, 128, 7442-7443;
29. d) V. B. Gondi, K. Hagihara, V. H. Rawal, Angew. Chem. 2009, 121, 790-793;
30. Angew. Chem. Int. Ed. 2009, 48, 776-779.
31. W. J. Pietro, W. J. Hehre, J. Am. Chem. Soc. 1982, 104, 3594-3595.
32. J. P. Abell, H. Yamamoto, J. Am. Chem. Soc. 2008, 130, 10521-10523.
33. For other examples of chiral base catalyzed hydrophosphonylation, see: a) H. Wynberg, A. A. Smaardijk, Tetrahedron Lett. 1983, 24, 5899-5900;
34. b) A. A. Smaardijk, S. Noorda, H. Wynberg, Tetrahedron Lett. 1985, 26, 493-496;
35. c) F. Wang, X. Liu, X. Cui, Y. Xiong, X. Zhou, X. Feng, Chem. Eur. J. 2009, 15, 589-592.
36. D. Uraguchi, T. Ito, T. Ooi, J. Am. Chem. Soc. 2009, 131, 3836-3837.
37. A. N. Pudovik, I. V. Konovalova, Synthesis 1979, 81-96.
38. a) B. Saito, T. Katsuki, Angew. Chem. 2005, 117, 4676-4678;
39. Angew. Chem. Int. Ed. 2005, 44, 4600-4602;
40. b) B. Saito, H. Egami, T. Katsuki, J. Am. Chem. Soc. 2007, 129, 1978-1986.
41. 3 accelerated the asymmetric hydrophosphinylation of imines without erosion of the enantio-selectivity: X. Fu, W-T. Loh, Y. Zhang, T. Chen, T. Ma, H. Liu, J. Wang, C.-H. Tan, Angew. Chem. 2009, 121, 7523-7526;
42. Angew. Chem. Int. Ed. 2009, 48, 7387-7390.
43. a) J. Takaki, H. Egami, K. Matsumoto, B. Saito, T. Katsuki, Chem. Lett. 2008, 37, 502-503;
44. b) H. Egami, H. Shimizu, T. Katsuki, Tetrahedron Lett. 2005, 46, 783-786;
45. c) H. Egami, R. Irie, K. Sakai, T. Katsuki, Chem. Lett. 2007, 36, 46-47.