The catalytic asymmetric abramov reaction

Angewandte Chemie - International Edition

Volumn 54, Issue 1, 2015, Pages 355-358

  Guin, Joyram ^a   Wang, Qinggang ^a   Van Gemmeren, Manuel ^a   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Abramov reaction; Disulfonimides; Hydrophosphonylations; Organocatalysis; hydroxy phosphonates

Indexed keywords

CATALYSTS; REACTION KINETICS;

ABRAMOV REACTION; DISULFONIMIDES; HYDROPHOSPHONYLATIONS; ORGANOCATALYSIS; PHOSPHONATES;

ENANTIOSELECTIVITY;

EID: 84920153803     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409411     Document Type: Article

References (73)

1. a) A. N. Pudovik, Dokl. Akad. Nauk SSSR 1950, 73, 499-502;
2. b) A. N. Pudovik, Y. O. Z. Kitaev, Zh. Obshch. Khim. 1952, 22, 467-473;
3. c) A. N. Pudovik, I. V. Konovalova, Synthesis 1979, 81-96;
4. d) D. Enders, A. Saint-Dizier, M.-I. Lannou, A. Lenzen, Eur. J. Org. Chem. 2006, 29-49.
5. a) A. Kraszewski, J. Stawinski, Pure. Appl. Chem. 2007, 79, 2217-2227;
6. b) J. Stawinski, A. Kraszewski, Acc. Chem. Res. 2002, 35, 952-960;
7. c) B. Stowasser, K.-H. Budt, L. Jian-Qi, A. Peyman, D. Ruppert, Tetrahedron Lett. 1992, 33, 6625-6628;
8. d) D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, Tetrahedron Lett. 1990, 31, 5587-5590;
9. e) D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, Tetrahedron Lett. 1990, 31, 5591-5594.
10. For recent reviews on catalytic enantioselective hydrophosphonylation reactions, see: a) D. Zhao, R. Wang, Chem. Soc. Rev. 2012, 41, 2095-2108;
11. b) P. Merino, E. Marqués-López, R. P. Herrera, Adv. Synth. Catal. 2008, 350, 1195-1208. For a recent organocatalytic example, see:
12. c) J. V. Alegre-Requena, E. Marqué s-López, P. J. S. Miguel, R. P. Herrera, Org. Biomol. Chem. 2014, 12, 1258-1264. For a more general review on catalytic methods to access organophosphorus compounds, see:
13. d) O. I. Kolodiazhnyi, V. P. Kukhar, A. O. Kolodiazhna, Tetrahedron: Asymmetry 2014, 25, 865-922.
14. a) F. Wang, X. Liu, X. Cui, Y. Xiong, X. Zhou, X. Feng, Chem. Eur. J. 2009, 15, 589-592;
15. b) D. Uraguchi, T. Ito, T. Ooi, J. Am. Chem. Soc. 2009, 131, 3836-3837;
16. c) A. A. Smaardijk, S. Noorda, F. van Bolhuis, H. Wynberg, Tetrahedron Lett. 1985, 26, 493-496;
17. d) H.Wynberg, A. A. Smaardijk, Tetrahedron Lett. 1983, 24, 5899-5900. For an alternative approach to this product class, see:
18. e) S. Samanta, S. Perera, C.-G. Zhao, J. Org. Chem. 2010, 75, 1101-1106. For selected examples of metal catalyzed enantioselective Pudovik reactions, see:
19. a) P. Muthupandi, G. Sekar, Org. Biomol. Chem. 2012, 10, 5347-5352;
20. b) K. Suyama, Y. Sakai, K. Matsumoto, B. Saito, T. Katsuki, Angew. Chem. Int. Ed. 2010, 49, 797-799;
21. Angew. Chem. 2010, 122, 809-811;
22. c) X. Zhou, X. Liu, X. Yang, D. Shang, J. Xin, X. Feng, Angew. Chem. Int. Ed. 2008, 47, 392-394;
23. Angew. Chem. 2008, 120, 398-400;
24. d) F. Yang, D. Zhao, J. Lan, P. Xi, L. Yang, S. Xiang, J. You, Angew. Chem. Int. Ed. 2008, 47, 5646-5649;
25. Angew. Chem. 2008, 120, 5728-5731;
26. e) S. Gou, X. Zhou, J. Wang, X. Liu, X. Feng, Tetrahedron 2008, 64, 2864-2870;
27. f) J. P. Abell, H. Yamamoto, J. Am. Chem. Soc. 2008, 130, 10521-10523;
28. g) B. Saito, H. Egami, T. Katsuki, J. Am. Chem. Soc. 2007, 129, 1978-1986;
29. h) B. Saito, T. Katsuki, Angew. Chem. Int. Ed. 2005, 44, 4600-4602;
30. Angew. Chem. 2005, 117, 4676-4678;
31. i) T. D. Nixon, S. Dalgarno, C. V. Ward, M. Jiang, M. A. Halcrow, C. Kilner, M. Thornton-Pett, T. P. Kee, C. R. Chim. 2004, 7, 809-821;
32. j) T. Yokomatsu, T. Yamagishi, S. Shibuya, J. Chem. Soc. Perkin Trans. 1 1997, 1527-1534;
33. k) H. Sasai, M. Bougauchi, T. Arai, M. Shibasaki, Tetrahedron Lett. 1997, 38, 2717-2720;
34. l) T. Arai, M. Bougauchi, H. Sasai, M. Shibasaki, J. Org. Chem. 1996, 61, 2926-2927;
35. m) N. P. Rath, C. D. Spilling, Tetrahedron Lett. 1994, 35, 227-230;
36. n) T. Yokomatsu, T. Yamagishi, S. Shibuya, Tetrahedron: Asymmetry 1993, 4, 1779-1782.
37. a)W. J. Pietro, W. J. Hehre, J. Am. Chem. Soc. 1982, 104, 3594-3595;
38. b) G. O. Doak, L. D. Freedman, Chem. Rev. 1961, 61, 31-44.
39. a) V. S. Abramov, Dokl. Akad. Nauk SSSR 1950, 73, 487-489;
40. b) V. S. Abramov, Dokl. Akad. Nauk SSSR 1954, 95, 991-992;
41. c) L. Woźniak, J. Chojnowski, Tetrahedron 1989, 45, 2465-2524.
42. For uncatalyzed diastereoselective hydrophosphonylations of chiral aldehydes with silyl phosphites, see: a) A. Bongini, R. Camerini, M. Panunzio, E. Bandini, G. Martelli, G. Spunta, Tetrahedron: Asymmetry 1996, 7, 3485-3504;
43. b) E. Bandini, G. Martelli, G. Spunta, M. Panunzio, Tetrahedron: Asymmetry 1995, 6, 2127-2130;
44. c) V. Sum, C. A. Baird, T. P. Kee, M. Thornton-Pett, J. Chem. Soc. Perkin Trans. 1 1994, 3183-3200;
45. d) N. Greene, T. P. Kee, Synth. Commun. 1993, 23, 1651-1657.
46. 4-mediated diastereoselective hydrophosphonylation of chiral aldehydes with silyl phosphites, see: e) T. Yokomatsu, Y. Yoshida, S. Shibuya, J. Org. Chem. 1994, 59, 7930-7933.
47. For an N-heterocyclic carbene-catalyzed hydrophosphonylation of aldehydes with silyl phosphites, see: f) Z.-H. Cai, G.-F. Du, L. He, C.-Z. Gu, B. Dai, Synthesis 2011, 2073-2078.
48. 4, and furnishes products with up to 76:24 e.r., see: K. Nakanishi, S. Kotani, M. Sugiura, M. Nakajima, Tetrahedron 2008, 64, 6415-6419.
49. D. A. Evans, K. M. Hurst, J. M. Takacs, J. Am. Chem. Soc. 1978, 100, 3467-3477.
50. a) P. García-García, F. Lay, P. García-García, C. Rabalakos, B. List, Angew. Chem. Int. Ed. 2009, 48, 4363-4366;
51. Angew. Chem. 2009, 121, 4427-4430;
52. b) L. Ratjen, P. García-García, F. Lay, M. E. Beck, B. List, Angew. Chem. Int. Ed. 2011, 50, 754-758;
53. Angew. Chem. 2011, 123, 780-784.
54. For reviews on ACDC, see: a) R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603-614;
55. b) K. Brak, E. N. Jacobsen, Angew. Chem. Int. Ed. 2013, 52, 534-561;
56. Angew. Chem. 2013, 125, 558-588;
57. c) M. Mahlau, B. List, Angew. Chem. Int. Ed. 2013, 52, 518-533;
58. Angew. Chem. 2013, 125, 540-556.
59. For a recent review on enantioselective catalysis using chiral enantiopure disulfonimides, see: a) M. van Gemmeren, F. Lay, B. List, Aldrichimica Acta 2014, 47, 3-13. For a kinetic study on the mechanism of disulfonimide-catalyzed reactions, see:
60. b) Z. Zhang, B. List, Asian J. Org. Chem. 2013, 2, 957-960.
61. For early studies highlighting the challenge of silylium ion background catalysis with silicon containing nucleophiles, see: a) E. M. Carreira, R. A. Singer, Tetrahedron Lett. 1994, 35, 4323-4326;
62. b) S. E. Denmark, C.-T. Chen, Tetrahedron Lett. 1994, 35, 4327-4330;
63. c) T. K. Hollis, B. Bosnich, J. Am. Chem. Soc. 1995, 117, 4570-4581;
64. d) C.-T. Chen, S.-D. Chao, K.-C. Yen, C.-H. Chen, I.-C. Chou, S.-W. Hon, J. Am. Chem. Soc. 1997, 119, 11341-11342.
65. It should be noted that the reaction conditions were optimized to maximize the enantiomeric ratio. Shorter reaction times can be achieved with slight loss of enantioselectivity by raising the temperature or increasing the catalyst loading. Likewise, reducing the equivalents of (trimethyl)silyl phosphite employed to 2.0 was possible with a slight loss of enantioselectivity. For details, see the SI.
66. K. Afarinkia, C.W. Rees, J. I. G. Cadogan, Tetrahedron 1990, 46, 7175-7196.
67. O. I. Kolodiazhnyi, Tetrahedron: Asymmetry 2012, 23, 1-46.
68. In one of our preceding studies we could show that the poor results obtained with aliphatic aldehydes are due to the formation of enol silanes under the reaction conditions as well as the significantly lower reactivity of these substrates requiring the reaction to be conducted at suboptimal conditions in terms of enantioselection. For details, see: M. Mahlau, P. García-García, B. List, Chem. Eur. J. 2012, 18, 16283-16287.
69. For rare examples of enantioselective Pudovik reactions with N-Boc imines, see: a) D. Pettersen, M. Marcolini, L. Bernardi, F. Fini, R. P. Herrera, V. Sgarzani, A. Ricci, J. Org. Chem. 2006, 71, 6269-6272;
70. b) J. George, B. Sridhar, B. V. S. Reddy, Org. Biomol. Chem. 2014, 12, 1595-1602. For an example involving the in situ generation of the N-Boc Imine, see:
71. c) F. Fini, G. Micheletti, L. Bernardi, D. Pettersen, M. Fochi, A. Ricci, Chem. Commun. 2008, 4345-4347. For nonenantioselctive reactions employing silyl dialkyl phosphites, see:
72. d) M. Hatano, S. Suzuki, E. Takagi, K. Ishihara, Tetrahedron Lett. 2009, 50, 3171-3174;
73. e) C. Zhihua, F. Yecheng, D. Guangfen, H. Lin, Chin. J. Chem. 2012, 30, 1658-1662.