Asymmetric allylation reactions of aromatic aldehydes with allyltrichlorosilane catalyzed by chiral bisformamide-type organocatalysts

Tetrahedron Asymmetry

Volumn 23, Issue 5, 2012, Pages 345-349

  Tanimura, Yuya ^a   Ishimaru, Kaori ^a  

^a NATIONAL DEFENSE ACADEMY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYLTRICHLOROSILANE; AMIDE; BENZALDEHYDE; BISFORMAMIDE; LEWIS BASE; N,N' BIS(9 ANTHRACENYLMETHYL) N,N' BISFORMYL 1,2 CYCLOHEXANEDIAMINE; N,N' BISFORMYL N,N' BIS(1 NAPHTHYLMETHYL) 1,2 CYCLOHEXANEDIAMINE; N,N' BISFORMYL N,N' BIS(2 ISOPROPYLBENZYL) 1,2 CYCLOHEXANEDIAMINE; N,N' BISFORMYL N,N' BIS(2 SEC BUTYLBENZYL) 1,2 CYCLOHEXANEDIAMINE; N,N' BISFORMYL N,N' BIS(2 TERT BUTYLBENZYL) 1,2 CYCLOHEXANEDIAMINE; N,N' BISFORMYL N,N' BIS(2,3 DIMETHYLBENZYL) 1,2 CYCLOHEXANEDIAMINE; N,N' BISFORMYL N,N' BIS(2,4,5 TRIMETHYLBENZYL) 1,2 CYCLOHEXANEDIAMINE; N,N' BISFORMYL N,N' BIS[2 (3,5 DIMETHYLPHENYL)BENZYL] 1,2 CYCLOHEXANEDIAMINE; N,N' DIBENZYL N FORMYL N' METHYL 1,2 CYCLOHEXANEDIAMINE; POTASSIUM CARBONATE; POTASSIUM DIHYDROGEN PHOSPHATE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ORGANOCATALYST; PRIORITY JOURNAL;

EID: 84860293466     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.02.015     Document Type: Article

References (36)

1. H. Yamamoto Lewis acids in Organic Synthesis 2001 Wiley-VCH Weinheim Vols. 1 and 2
2. S.E. Denmark, and J. Fu Chem. Rev. 103 2003 2763 2793
3. Y. Orito, and M. Nakajima Synthesis 2006 1391 1401
4. S.E. Denmark, and G.L. Beutner Angew. Chem., Int. Ed. 47 2008 1560 1638
5. K. Iseki, S. Mizuno, Y. Kuroki, and Y. Kobayashi Tetrahedron Lett. 39 1998 2767 2770
6. K. Iseki, S. Mizuno, Y. Kuroki, and Y. Kobayashi Tetrahedron 55 1999 977 988
7. S.E. Denmark, D.M. Coe, N.E. Pratt, and B.D. Griedel J. Org. Chem. 59 1994 6161 6163 for recent papers, see
8. S.E. Denmark, J. Fu, D.M. Coe, X. Su, N.E. Pratt, and B.D. Griedel J. Org. Chem. 71 2006 1513 1522
9. T. Nemoto, T. Hitomi, H. Nakamura, L. Jin, and K. Hatano Hamada Y. Tetrahedron: Asymmetry 18 2007 1844 1849
10. S.E. Denmark, and J.J. Fu Am. Chem. Soc. 122 2000 12021 12022
11. S.E. Denmark, and J.J. Fu Am. Chem. Soc. 123 2001 9488 9489
12. S.E. Denmark, J. Fu, and M.J.J. Lawler Org. Chem. 71 2006 1523 1536
13. S. Kobayashi, C. Ogawa, H. Konishi, and M.J. Sugiura Am. Chem. Soc. 125 2003 6610 6611
14. A. Massa, A.V. Malkov, P. Kočovský, and A. Scettri Tetrahedron Lett. 44 2003 7179 7181
15. V. De Sio, A. Massa, and A. Scettri Org. Biomol. Chem. 8 2010 3055 3059
16. V. De Sio, M.R. Acocella, R. Villano, and A. Scettri Tetrahedron: Asymmetry 21 2010 1432 1435
17. F. García-Flores, L.S. Flores-Michel, and E. Juaristi Tetrahedron Lett. 47 2006 8235 8238
18. A. Massa, M.R. Acocella, V. De Sio, R. Villano, and A. Scettri Tetrahedron: Asymmetry 20 2009 202 204 see also ref 6d.
19. A.V. Malkov, M. Orsini, D. Pernazza, K.W. Muir, V. Langer, P. Meghani, and P. Kočovský Org. Lett. 4 2002 1047 1049 for recent reports, see
20. L. Pignataro, M. Benaglia, R. Annunziata, M. Cinquini, and F. Cozzi J. Org. Chem. 71 2006 1458 1463
21. V. Simonini, M. Benaglia, L. Pignataro, S. Guizzetti, and G. Celentano Synlett 2008 1061 1065
22. A.V. Malkov, M. Barlóg, Y. Jewkes, J. Mikušek, and P. Kočovský J. Org. Chem. 76 2011 4800 4804
23. M. Nakajima, M. Saito, M. Shiro, and S. Hashimoto J. Am. Chem. Soc. 120 1998 6419 6420
24. M. Nakajima, M. Saito, and S. Hashimoto Chem. Pharm. Bull. 48 2000 306 307
25. T. Shimada, A. Kina, S. Ikeda, and T. Hayashi Org. Lett. 4 2002 2799 2801 for recent reports, see
26. R. Hrdina, T. Boyd, I. Valterová, J. Hodačová, and M. Kotora Synlett 2008 3141 3144
27. Y.S. Oh, S. Kotani, M. Sugiura, and M. Nakajima Tetrahedron: Asymmetry 21 2010 1833 1835
28. A.V. Malkov, O. Kysilka, M. Edgar, A. Kadlčíková, M. Kotora, and P. Kočovský Chem. Eur. J. 17 2011 7162 7166
29. W.-L. Wong, C.-S. Lee, H.-K. Leung, and H.-L. Kwong Org. Biomol. Chem. 2 2004 1967 1969
30. C. Ogawa, M. Sugiura, and S. Kobayashi Angew. Chem., Int. Ed. 43 2004 6491 6493
31. C. Ogawa, H. Konishi, M. Sugiura, and S. Kobayashi Org. Biomol. Chem. 2 2004 446 448
32. M. Nakajima, S. Kotani, T. Ishizuka, and S. Hashimoto Tetrahedron Lett. 46 2005 157 159
33. S. Kotani, S. Hashimoto, and M. Nakajima Tetrahedron 63 2007 3122 3132
34. K. Ishimaru, K. Ono, Y. Tanimura, and T. Kojima Syn. Commun. 41 2011 3627 3634
35. L.I. Krimen Org. Synth. 6 1988 8
36. 1H NMR spectra of the chiral bisformamides show a mixture of rotamers, see the Supplementary data in the reference. S.E. Denmark, X. Su, Y. Nishigaichi, D.M. Coe, K.-T. Wong, S.B.D. Winter, and J.Y. Choi J. Org. Chem. 64 1999 1958 1967