Highly enantioselective 1,4- addition of diethyl phosphite to enones using a dinuclear Zn catalyst

Chemistry - A European Journal

Volumn 15, Issue 12, 2009, Pages 2738-2741

  Zhao, Depeng ^a   Yuan, Ye ^a   Chan, Albert S C ^b   Wang, Rui ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Asymmetric catalysis; Enones; Hydrophosphosphonylation; Michael addition; Phosphonates

Indexed keywords

ALCOHOLS; AMINES; AROMATIC HYDROCARBONS; CATALYSIS; CATALYSTS; ENANTIOSELECTIVITY; ZINC;

ASYMMETRIC CATALYSIS; ENONES; HYDROPHOSPHOSPHONYLATION; MICHAEL ADDITION; PHOSPHONATES;

ADDITION REACTIONS;

KETONE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; PHOSPHORYLATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; KETONES; MOLECULAR STRUCTURE; PHOSPHITES; PHOSPHONIC ACIDS; PHOSPHORYLATION; STEREOISOMERISM; ZINC;

EID: 62349128115     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802688     Document Type: Article

References (65)

1. For a recent review of the asymmetric synthesis of α-hydroxy and α-amino phosphonates see: a) P. Merino. E. Marqués-López, R. P. Herrera. Adv. Synth. Catal. 2008, 350, 1195-1208;
2. for recent examples of the synthesis of chiral phosphonates, see: b) J. P. Abell, H. Yamamoto, J. Am. Chem. Soc. 2008, 130, 10521-10523;
3. c) X. Zhou, X. Liu, X. Yang, D. Shang, J. Xin, X. Feng. Angew. Chem. 2008, 120, 398-400;
4. Angew. Chem. Int. Ed. 2008, 47, 392-394;
5. d) F. Yang, D. Zhao, J. Lan, P. Xi, L. Yang, S. Xiang, J. You, Angew. Chem. 2008, 120, 5728-5731;
6. Angew. Chem. Int. Ed. 2008, 47, 5646-5649;
7. e) B. Saito, H. Egami, T. Katsuki, J. Am. Chem. Soc. 2007, 129, 1978-1986;
8. f) Z. Duan, X. Hu, D. Wang. J. Huang, S. Yu, J. Deng, Z. Zheng, Adv. Synth. Catal. 2008, 350, 1979-1983;
9. g) K. Barta, G. Franciò, W. Leitner, G. C. Lloyd-Jones, I. R. Shepperson, Adv. Synth. Catal. 2008, 350, 2013-2023.
10. a) The role of phosphonates in living systems, (Ed.: R. L. Hilde-brand). CRC Press, Boca Raton, 1983;
11. b) R. Engel. Chem. Rev. 1977, 77, 349-367;
12. c) K. Moonen, I. Laureyn, C. V. Stevens, Chem. Rev. 2004, 104, 6177-6216;
13. d) F. Palacios, C. Alonso. J. M. de Los Santos, Chem. Rev. 2005, 105, 899-932;
14. e) J. A. Ma, Chem. Soc. Rev. 2006, 35, 630-636;
15. f) V. D. Romanenko, V. P. Kukhar. Chem. Rev. 2006, 106, 3868-3935.
16. For a review of 1,4-addition reactions of phosphorus nucleophiles with electron-deficient alkenes, see: D. Enders, A. Saint-Dizier, M.-I. Lannou, A. Lenzen, Eur. J. Org. Chem. 2006, 29-49.
17. For examples of catalytic asymmetric addition of disubstituted phosphite to electron-deficient alkenes, see: a) J. Wang. L. D. Heikkinen, H. Li, L. Zu, W. Jiang, H. Xie, W. Wang. Adv. Synth. Catal. 2007, 349, 1052-1056;
18. b) M. Terada, T. Ikehara, H. Ube, J. Am. Chem. Soc. 2007, 129, 14112-14113;
19. c) E. Maerten. S. Cabrera, A. Kjarsgaard. K. A. Jørgensen. J. Org. Chem. 2007. 72, 8893-8903.
20. For examples of asymmetric addition of phosphite to electron-deficient alkenes using chiral substrates, see: d) H. Paulsen, W. Greve, Chem. Ber. 1973, 106. 2114-2123;
21. e) H. Yamamoto, T. Hanaya, H. Kawamoto, S. Inokawa, M. Yamashila, M. A. Armour. T. T. Nakashima, J. Org. Chem. 1985, 50, 3516-3521;
22. f) M. Yamashita. M. Sugiura, Y. Tamada, T. Oshikawa, J. Clardy. Chem. Lett. 1987, 1407-1408;
23. g) O. I. Kolodiazhnyi. S. Sheiko, E. V. Grishkun. Heteroat. Chem. 2000, 11, 138-143;
24. h) G. Caslelol-Deliencourt, X. Pannecoucke, J.-C. Quirion, Tetrahedron Lett. 2001, 42. 1025-1028;
25. i) L. Tedeschi, D. Enders, Org. Lett. 2001. 3, 3515-3517:
26. j) D. Enders, L. Tedeschi, J W. Bats, Angew. Chem. 2000, 112, 4774-4776;
27. Angew. Chem. Int. Ed. 2000, 39, 4605-4607;
28. k) D. Enders. L. Tedeschi, D. Foster, Synthesis 2006. 1447-1460.
29. For examples of the catalytic asymmetric hydrophosphination of electron-deficient alkenes, see: a) G. Barloli, M. Bosco, A. Carlone, M. Localelli, A. Mazzanti. L. Sambri, P. Melchiorre. Chem. Commun. 2007, 722-724:
30. b) A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Angew. Chem. 2007, 119, 4588-4590;
31. Angew. Chem. Int. Ed. 2007. 46, 4504-4506:
32. c) I. Ibrahem, R. Rios, J. Vesely, P. Hammar, L. Eriksson. F. Himo, A. Córdova, Angew. Chem. 2007, 119, 4591-4594;
33. Angew. Chem. Int. Ed. 2007, 46, 4507-4510;
34. d) I. Ibrahem, P. Hammar, J. Vesely, R. Rios, L. Eriksson. A. Córdova, Adv. Synth. Catal. 2008. 350, 1875-1884;
35. e) X. Fu. Z. Jiang, C.-H. Tan, Chem. Commun. 2007, 5058-5060;
36. f) A. D. Sadow, I. Haller, L. Fadini, A. Togni, J. Am. Chem. Soc. 2004, 126. 14704-14705;
37. g) A. D. Sadow. A. Togni, J. Am. Chem. Soc. 2005. 127, 17012-17024.
38. For a review of reactions catalyzed by cinchona alkaloids, see: S.-K. Tian, Y.-G. Chen, J.-F. Hang. L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621.
39. For a review of chiral guanidine catalysts, see: a) T. Ishikawa, T. Isobe, Chem. Eur. J. 2002, 8, 552-557.
40. a) D. Enders, L. Tedeschi, J.W. Bats, Angew. Chem. 2000, 112, 4774-4776;
41. Angew. Chem. Int. Ed. 2000, 39, 4605-4607;
42. b) J. Boersma, J. G. Noltes, Reel. Trav. Chim. Pays-Bas. 1973, 92, 229-236.
43. For reviews of chiral amino alcohols in asymmetric synthesis, see: a) S. M. Lait, D. A. Rankic, B. A. Keay, Chem. Rev. 2007, 107, 767-796;
44. b) L. Pu, H.-B. Xu, Chem. Rev. 2001, 101, 757-824.
45. For recent examples from our group on reactions catalyzed by chiral amino alcohols, see: c) Z. Q. Xu, R. Wang, J. K. Xu, C. S. Da, W. J. Yan, C. Chen, Angew. Chem. 2003, 115, 5925-5927;
46. Angew. Chem. Int. Ed. 2003, 42, 5747-5749;
47. d) Z. Xu, C. Chen, J. Xu, M. Miao, W. Yan, R. Wang, Org. Lett. 2004, 6, 1193-1195;
48. e) C. Chen, L. Hong, Z.-Q. Xu, L. Liu, R. Wang, Org. Lett. 2006, 8, 2277-2280;
49. f) Y.-F. Kang, L. Liu, R. Wang, W.-J. Yan, Y.-F. Zhou, Tetrahedron: Asymmetry 2004, 15, 3155-3159;
50. g) L. Lin, X. Jiang, W. Liu, L. Qiu, Z. Xu, J. Xu, A. S. C. Chan, R. Wang, Org. Lett. 2007, 9, 2329-2332.
51. Further lowering the temperature to -40°C led to no reaction.
52. For aldol reactions, see: a) B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003-12004;
53. b) B. M. Trost, H. Ito, E. R. Silcoff, J. Am. Chem. Soc. 2001, 123, 3367-3368;
54. c) B. M. Trost, A. Fettes, B. T. Shireman, J. Am. Chem. Soc. 2004, 126, 2660-2661;
55. d) B. M. Trost, S. Shin, J. A. Sclafani, J. Am. Chem. Soc. 2005, 127, 8602-8603;
56. for Mannich reactions, see: e) B. M. Trost, J. Jaratjaroonphong, V. Reutrakul, J. Am. Chem. Soc. 2006, 128, 2778-2779;
57. f) B. M. Trost, L. R. Terrell, J. Am. Chem. Soc. 2003, 125, 338-339; for nitroaldol reactions, see:
58. g) B.M. Trost, D.W. Lupton, Org. Lett. 2007, 9, 2023-2026;
59. h) B.M. Trost, B. M. V. S. C. Yeh, Angew. Chem. 2002, 114, 889-891;
60. Angew. Chem. Int. Ed. 2002, 41, 861-863;
61. for desymmetrizations, see: i) B. M. Trost, T. Mino, J. Am. Chem. Soc. 2003, 125, 2410-2411;
62. j) B. M. Trost, S. Malhotra, T. Mino, N.S. Rajapaksa, Chem. Eur. J. 2008, 14, 7648-7657;
63. for Friedel-Crafts reaction, see: k) B. M. Trost, C. Muller, J. Am. Chem. Soc. 2008, 130, 2438-2439.
64. α-Alkyl enones were also examined, and only 1,2-phosphite addition adducts were observed.
65. S. Gardner, K. Shastri, A. C. Sullivan, P. B. Wyatt, New J. Chem. 2002, 26, 433-439.