Development of chiral dinitrones as modular Lewis base catalysts: Asymmetric allylation of aldehydes with allyltrichlorosilanes

Tetrahedron Asymmetry

Volumn 21, Issue 15, 2010, Pages 1833-1835

  Seon Oh, Young ^a   Kotani, Shunsuke ^a   Sugiura, Masaharu ^a   Nakajima, Makoto ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BENZALDEHYDE; CHLOROFORM; LEWIS BASE; NITRONE; SILANE;

ALLYLATION; ARTICLE; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; POLYMERIZATION; PRIORITY JOURNAL; ROOM TEMPERATURE; SCREENING; SYNTHESIS;

EID: 77957578700     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.05.048     Document Type: Article

References (48)

1. For recent reviews on modular ligands or catalysts, see: Reetz, M. T. Angew. Chem., Int. Ed. 2008, 47, 2556-2588
2. Blaser, H.-U.; Pugin, B.; Spindler, F.; Thommen, M. Acc. Chem. Res. 2007, 40, 1240-1250
3. Hoveyda, A. H.; Hird, A. W.; Kacprzynski, M. A. Chem. Commun. 2004, 1779-1785.
4. Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419-6420
5. Nakajima, M.; Yokota, T.; Saito, M.; Hashimoto, S. Tetrahedron Lett. 2004, 45, 61-64
6. Nakajima, M.; Kotani, S.; Ishizuka, T.; Hashimoto, S. Tetrahedron Lett. 2005, 46, 157-159
7. Kotani, S.; Hashimoto, S.; Nakajima, M. Synlett 2006, 1116-1118
8. Kotani, S.; Hashimoto, S.; Nakajima, M. Tetrahedron 2007, 63, 3122-3132
9. Nakanishi, K.; Kotani, S.; Sugiura, M.; Nakajima, M. Tetrahedron 2008, 64, 6415-6419
10. Sugiura, M.; Sato, N.; Kotani, S.; Nakajima, M. Chem. Commun. 2008, 4309-4311
11. Sugiura, M.; Kumahara, M.; Nakajima, M. Chem. Commun. 2009, 3585-3587
12. Kotani, S.; Shimoda, Y.; Sugiura, M.; Nakajima, M. Tetrahedron Lett. 2009, 50, 4602-4605;
13. Shimoda, Y.; Tando, T.; Kotani, S.; Sugiura, M.; Nakajima, M. Tetrahedron: Asymmetry 2009, 20, 1369-1370
14. Sugiura, M.; Sato, N.; Sonoda, Y.; Kotani, S.; Nakajima, M. Chem. Asian J. 2010, 5, 478-781.
15. For reviews on Lewis base catalysis, see: Orito, Y.; Nakajima, M. Synthesis 2006, 1391-1401
16. Malkov, A. V.; Kocovský, P. Eur. J. Org. Chem. 2007, 29-36;
17. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008 47 1560-1638
18. Liu, X.; Lin, L.; Feng, X. Chem. Commun. 2009, 6145-6158.
19. For reviews, see: Pellissier, H. Tetrahedron 2007, 63, 3235-3285
20. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863-909
21. Merino, P. C. P. Chimie 2005, 8, 775-788
22. Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442-454
23. Lombaro, M.; Trombini, C. Synthesis 2000, 759-774
24. For recent examples of nitrone ligands for metal-catalysts, see: Yao, Q.; Zabawa, M.; Woo, J.; Zheng, C. J. Am. Chem. Soc. 2007, 129, 3088-3089
25. Zhang, Y.; Song, G.; Ma, G.; Zhao, J.; Pan, C.-L.; Li, X. Organometllics 2009, 28, 3233-3238.
26. C2-Symmetrical bisimidazole N,N0-dioxides derived from 1,2- cyclohaxanediamine have recently been reported as Lewis base catalysts for enantioselective allylation, see: Kwiatkowski, P.; Mucha, P.; Mloston , G.; Jurczak, J. Synlett 2009, 1757-1760.
27. Zhang, W.; Basak, A.; Kosugi, Y.; Hoshino, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 4389-4391.
28. General procedure for preparation of dinitrones: To (S,S)-N,N- dihydroxyl1-1,2-cyclohexanediamine dihydrochloride7 (0.5 mmol), dichloromethane (10 mL), NaHCO3 (252 mg, 6 equiv), and an aldehyde (1.5 mmol) were added at room temperature. The reaction mixture was refluxed for 6 h, filtered, and evaporated. The residue was purified by silica gel column chromatography (hexane/acetone or dichloromethane/EtOH) to give a dinitrone.
29. Leading references on enantioselective allylation of aldehydes with allyltrichlorosilanes catalyzed by various types of chiral Lewis bases. For chiral phosphoramides, see: Denmark, S. E.; Coe D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59 6161-6163
30. Denmark, S. E.; Fu, J.; Lawler, M. J. J. Org. Chem. 2006, 71, 1523-1536
31. For chiral pyridine N-oxides, see: Ref. 2a.
32. Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovský, P. Org. Lett. 2002, 4, 1047-1049
33. Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799-2801
34. Malkov, A. V.; Bell, M.; Castelluzzo, F.; Kocovský, P. Org. Lett. 2005, 7, 3219-3222
35. Chai, Q.; Song, C.; Sun, Z.; Ma, Y.; Ma, C.; Dai, Y.; Andrus, M. B. Tetrahedron Lett. 2006, 47, 8611-8615
36. Kadlcikova, A.; Hrdina, R.; Valterova, I.; Kotora, M. Adv. Synth. Catal. 2009, 351, 1279-1283
37. For chiral formamides, see: Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767-2770
38. For chiral sulfoxides, see: Massa, A.; Malkov, A. V.; Kocovský , P.; Scettri, A. Tetrahedron Lett. 2003, 44, 7179-7181
39. Rowlands, G. J.; Barnes, W. K. Chem. Commun. 2003, 9, 2712-2713
40. For chiral phosphine oxides, see: Ref. 2c.
41. Simonini, V.; Benaglia, M.; Benincori, T. Adv. Synth. Catal. 2008, 350, 561-564
42. For chiral pyrrolidine Noxides, see: Traverse, J. F.; Zhao, Y.; Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2005, 7, 3151-3154
43. Simonini, V.; Benaglia, M.; Pignataro, L.; Guizzetti, S.; Celentano, G. Synlett 2008, 1061-1065.
44. DMPU and chiral urea derivatives have been used for allylation with allyltrichlorosilane, see: Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633-3634.
45. HMPA has been used as an effective achiral additive for enantioselective allylation catalyzed by chiral formamides, see: Ref. 9i.
46. Catalyst 1a (Table 3, entry 1) and 1f (entry 10) were recovered in 99% and 93%, respectively.
47. General procedure for allylation of aldehydes with allyltrichlorosilanes: to a solution of dinitrone 1f (20 mol %), an aldehyde 2 (0.4 mmol), and DMPU (1.5 equiv) in chloroform (1 mL) was added allyltrichlorosilane (1.5 equiv) under argon at room temperature. After being stirred at that temperature for 24 h, the reaction was quenched with satd aqueous NaHCO3 (10 mL), and the slurry was stirred for 1 h. The mixture was filtered through cotton wool and extracted with ethyl acetate (3- 15 mL). The combined organic layers were washed with brine (1- 30 mL), dried over MgSO4, filtered, and concentrated under vacuum. The crude product was purified by silica gel column chromatography (hexane/ ethyl acetate) to give the product The enantiomeric excess was determined by HPLC analysis.
48. Low reactivity of non-conjugated aldehydes has been observed for Lewis basecatalyzed reactions with trichlorosilylated reagents. This result has been ascribed to the formation of the corresponding O-silylated chlorohydrins, see: Denmark, S. E.; Wynn, T.; Beutner, G. L. J. Am. Chem. Soc. 2002, 124, 13405-13407.