Enantioselective cyanosilylation of aldehydes catalyzed by a novel N,N′-dioxide-Ti(OiPr)4 bifunctional catalyst

Tetrahedron

Volumn 63, Issue 24, 2007, Pages 5129-5136

  Zeng, Baiqing ^a   Zhou, Xin ^a   Liu, Xiaohua ^a   Feng, Xiaoming ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Bifunctional catalyst; Cyanosilylation; Lewis acid; Lewis base

Indexed keywords

1 [(1 OXIDOPYRIDIN 2 YL)METHYL] 2 (ARYLCARBAMOYL)OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 1 [(1 OXIDOPYRIDIN 2 YL)METHYL] 2 (PHENYLCARBAMOYL)OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 1 [(1 OXIDOPYRIDIN 2 YL)METHYL] 2 (PHENYLETHYLCARBAMOYL)OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 2 (2 METOXYPHENYLCARBAMOYL) 1 [(1 OXIDOPYRIDIN 2 YL)METHYL]OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 2 (2 TERT BUTYLPHENYLCARBAMOYL) 1 [(1 OXIDOPYRIDIN 2 YL)METHYL]OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 2 (2,6 DIIDOPROPYLPHENYLCARBAMOYL) 1 [(1 OXIDOPYRIDIN 2 YL)METHYL]OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 2 (BENZHYDRYLCARBAMOYL) 1 ( PYRIDIN 2 YLMETHYL)OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 2 (BENZHYDRYLCARBAMOYL) 1 [(1 OXIDOPYRIDIN 2 YL)METHYL]OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 2 (BENZHYDRYLCARBAMOYL) 1 BENZYL OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 2 (BENZYLCARBAMOYL) 1 [(1 OXIDOPYRIDIN 2 YL)METHYL]OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 2 (CYCLOHEXYLCARBAMOYL) 1 [(1 OXIDOPYRIDIN 2 YL)METHYL]OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 2 ADANACARBAMOYL 1 [(1 OXIDOPYRIDIN 2 YL)METHYL]OCTAHYDROCYCLOPENTA[B]PYRROLE 1 OXIDE; 2 HDYROXY 2 (1'NAPHTHYL)ACETONITRILE; 2 HYDROXY 2 (2 CHLOROPHENYL)ACETONITRILE; 2 HYDROXY 2 (3 CHLOROPHENYL)ACETONITRILE; 2 HYDROXY 2 (3 METHYLPHENYL)ACETONITRILE; 2 HYDROXY 2 (4 CHLOROPHENYL)ACETONITRILE; 2 HYDROXY 2 (4 FLUOROPHENYL)ACETONITRILE; 2 HYDROXY 2 (4 METHYLPHENYL)ACETONITIRILE; 2 HYDROXY 2 (FLUOROPHENYL)ACETONITRILE; 2 HYDROXY 2 (METHOXYPHENYL)ACETONITRILE; 2 HYDROXY 2 PHENYLACETONITRILE; 2 HYDROXYHEPTANENITRILE; ALDEHYDE DERIVATIVE; CYANOHYDRIN; LEWIS ACID; N ARYL ALKYL 1 (PYRIDIN 2 YL METHYL)OCTAHYDROCYCLOPENTAL[B]PYRROLE 2 CARBOXAMIDE; TITANIUM DERIVATIVE; TRIMETHYLSILYL CYANOHYDRIN; TRIMETHYLSILYLCYANIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; OPTICAL ROTATION; PRIORITY JOURNAL;

EID: 34247896945     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.04.008     Document Type: Article

References (60)

1. Effenberger F., and Stelzer U. Angew. Chem., Int. Ed. Engl. 30 (1991) 873-874
2. Zandbergen P., Brussee J., Van der Gen A., and Kruse C.G. Tetrahedron: Asymmetry 3 (1992) 769-774
3. Matthews B.R., Gountzos H., Jackson W.R., and Watson K.G. Tetrahedron Lett. 30 (1989) 5157-5158
4. Ziegler T., Hoersch B., and Effenberger F. Synthesis (1990) 575-578
5. Jackson W.R., Jacobs H.A., Jayatilake G.S., Matthews B.R., and Watson K.G. Aust. J. Chem. 43 (1990) 2045-2062
6. Jackson W.R., Jacobs H.A., Matthews B.R., Jayatilake G.S., and Watson K.G. Tetrahedron Lett. 31 (1990) 1447-1450
7. For some examples using chiral metal complexes, see:
8. Corey E.J., and Wang Z. Tetrahedron Lett. 34 (1993) 4001-4004
9. Holmes I.P., and Kagan H.B. Tetrahedron Lett. 41 (2000) 7453-7456
10. Holmes I.P., and Kagan H.B. Tetrahedron Lett. 41 (2000) 7457-7460
11. Trost B.M., and Martinez-Sanchez S. Synlett (2005) 627-630
12. Kim S.S., and Song D.H. Eur. J. Org. Chem. (2005) 1777-1780
13. Ooi T., Takaya K., Miura T., Ichikawa H., and Maruoka K. Synlett (2000) 1133-1134
14. Brunel J., Legrand O., and Buono G. Tetrahedron: Asymmetry 10 (1999) 1979-1984
15. Yang Z., Zhou Z., Wang L., Li K., Zhou Q., and Tang C. Synth. Commun. 32 (2002) 2751-2756
16. Yang Z., Zhou Z., He K., Wang L., Zhao G., Zhou Q., and Tang C. Tetrahedron: Asymmetry 14 (2003) 3937-3941
17. He K., Zhou Z., Wang L., Li K., Zhao G., Zhou Q., and Tang C. Tetrahedron 60 (2004) 10505-10513
18. He K., Zhou Z., Wang L., Li K., Zhao G., Zhou Q., and Tang C. Synlett (2004) 1521-1524
19. For some examples using organocatalysts, see:
20. Kitani Y., Kumamoto T., Isobe T., Fukuda K., and Ishikawa T. Adv. Synth. Catal. 347 (2005) 1653-1658
21. Wen Y., Huang X., Huang J., Xiong Y., Qin B., and Feng X. Synlett (2005) 2445-2448
22. Denmark S.E., and Chung W. J. Org. Chem. 71 (2006) 4002-4005
23. Bolm C., and Muller P. Tetrahedron Lett. 36 (1995) 1625-1628
24. Mori M., Imma H., and Nakai T. Tetrahedron Lett. 38 (1997) 6229-6232
25. Sellner H., Faber C., Rheiner P.B., and Seebach D. Chem.-Eur. J. 6 (2000) 3692-3705
26. Tian J., Yamagiwa N., Matsunaga S., and Shibasaki M. Angew. Chem., Int. Ed. 41 (2002) 3636-3638
27. Shibasaki M., Kanai M., and Funabashi K. Chem. Commun. (2002) 1989-1999
28. Hamashima Y., Sawada D., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 121 (1999) 2641-2642
29. Hamashima Y., Sawada D., Nogami H., Kanai M., and Shibasaki M. Tetrahedron 57 (2001) 805-814
30. Casas J., Najera C., Sansano J.M., and Saa J.M. Org. Lett. 4 (2002) 2589-2592
31. Qian C., Zhu C., and Huang T. J. Chem. Soc., Perkin Trans. 1 (1998) 2131-2132
32. Qin Y., Liu L., and Pu L. Org. Lett. 7 (2005) 2381-2383
33. Ooi T., Miura T., Takaya K., Ichikawa H., and Maruoka K. Tetrahedron 57 (2001) 867-873
34. Minamikawa H., Hayakawa S., Yamada T., Iwasawa N., and Narasaka K. Bull. Chem. Soc. Jpn. 61 (1988) 4379-4383
35. Narasaka K., Yamada T., and Minamikawa H. Chem. Lett. (1987) 2073-2076
36. Abiko A., and Wang G. J. Org. Chem. 61 (1996) 2264-2265
37. Abiko A., and Wang G. Tetrahedron 54 (1998) 11405-11420
38. Kanai M., Hamashima Y., and Shibasaki M. Tetrahedron Lett. 41 (2000) 2405-2409
39. Callant D., Stanssens D., and De Vries J.G. Tetrahedron: Asymmetry 4 (1993) 185-188
40. Iovel I., Popelis Y., Fleisher M., and Lukevics E. Tetrahedron: Asymmetry 8 (1997) 1279-1285
41. Aspinall H.C., Greeves N., and Smith P.M. Tetrahedron Lett. 40 (1999) 1763-1766
42. Yang W., and Fang J. J. Org. Chem. 63 (1998) 1356-1359
43. Hwang C., Hwang D., and Uang B. J. Org. Chem. 63 (1998) 6762-6763
44. Ryu D.H., and Corey E.J. J. Am. Chem. Soc. 126 (2004) 8106-8107
45. Li Y., He B., Qin B., Feng X., and Zhang G. J. Org. Chem. 69 (2004) 7910-7913
46. Lee P., and Chen C. Tetrahedron: Asymmetry 16 (2005) 2704-2710
47. Kim Y.B., Kim M.K., Kang S.H., and Kim Y.H. Synlett (2005) 1995-1998
48. Uang B., Fu I., Hwang C., Chang C., Yang C., and Hwang D. Tetrahedron 60 (2004) 10479-10486
49. Chen F., Feng X., Qin B., Zhang G., and Jiang Y. Org. Lett. 5 (2003) 949-952
50. Chen F., Zhou H., Liu X., Qin B., Feng X., Zhang G., and Jiang Y. Chem.-Eur. J. 10 (2004) 4790-4797
51. Chen F., Qin B., Feng X., Zhang G., and Jiang Y. Tetrahedron 60 (2004) 10449-10460
52. Shen Y., Feng X., Zhang G., and Jiang Y. Synlett (2002) 1353-1355
53. Shen Y., Feng X., Li Y., Zhang G., and Jiang Y. Eur. J. Org. Chem. (2004) 129-137
54. Schmidt M., Herve S., Klempier N., and Griengl H. Tetrahedron 52 (1996) 7833-7840
55. Inagaki M., Hiratake J., Nishioka T., and Oda J. J. Org. Chem. 57 (1992) 5643-5649
56. Steele R.M., Monti C., Gennari C., Piarulli U., Andreoli F., Vanthuyne N., and Roussel C. Tetrahedron: Asymmetry 17 (2006) 999-1006
57. Matthews B.R., Jackson W.R., Jayatilake G.S., Wilshire C., and Jacobs H. Aust. J. Chem. 41 (1988) 1697-1709
58. Liu Y., Liu X., Xin J., and Feng X. Synlett (2006) 1085-1089
59. Xiong Y., Huang X., Gou S., Huang J., Wen Y., and Feng X. Adv. Synth. Catal. 348 (2006) 538-544
60. O'Neil I.A., Miller N.D., Peake J., Barkley J.V., Low C.R., and Kalindjian S.B. Synlett (1993) 515-518