The first allylation of imines with allyltrichlorosilanes using neutral coordinate-organocatalysts

Synlett

Volumn , Issue 11, 2003, Pages 1749-1751

  Sugiura, Masaharu ^a   Robvieux, Fabrice ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Allylations; Catalysis; Imines; Neighboring group effects; Stereoselective

Indexed keywords

2 AMINOPHENOL; ALDEHYDE DERIVATIVE; HEMPA; IMINE; N,N DIMETHYLFORMAMIDE; PYRIDINE 1 OXIDE; SILANE DERIVATIVE;

ALLYLATION; ARTICLE; CATALYST; CHEMICAL MODIFICATION; DEPROTECTION REACTION; EPIMERIZATION; STEREOCHEMISTRY;

EID: 0041910844     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41437     Document Type: Article

References (22)

1. For recent reviews on allylmetal additions: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (f) Yamamoto, Y.; Asano, N. Chem. Rev. 1993, 93, 2207.
2. For recent reviews on allylmetal additions: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (f) Yamamoto, Y.; Asano, N. Chem. Rev. 1993, 93, 2207.
3. For recent reviews on allylmetal additions: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (f) Yamamoto, Y.; Asano, N. Chem. Rev. 1993, 93, 2207.
4. For recent reviews on allylmetal additions: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (f) Yamamoto, Y.; Asano, N. Chem. Rev. 1993, 93, 2207.
5. For recent reviews on allylmetal additions: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (f) Yamamoto, Y.; Asano, N. Chem. Rev. 1993, 93, 2207.
6. For recent reviews on allylmetal additions: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000, Chap. 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (f) Yamamoto, Y.; Asano, N. Chem. Rev. 1993, 93, 2207.
7. (a) Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1993, 34, 3453.
8. (b) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
9. (c) Ogawa, C.; Sugiura, M.; Kobayashi, S. Chem. Commun. 2003, 192; and references therein.
10. (a) Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942.
11. (b) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493.
12. (c) Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Org. Chem. 2002, 67, 5359.
13. (d) Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 6610; and references therein.
14. We have successfully utilized 2-aminophenols-derived imines for chiral zirconium-catalyzed asymmetric reactions. For leading references, see: (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180. (b) Mannich-type reaction: Kobayashi, S.; Kobayashi, J.; Ishitani, H.; Ueno, M. Chem.-Eur. J. 2002, 8, 4185. (c) Allylation using allyltributyltins: Gastner, T.; Ishitani, H.; Kobayashi, S. Angew. Chem. Int. Ed. 2001, 40, 1896.
15. We have successfully utilized 2-aminophenols-derived imines for chiral zirconium-catalyzed asymmetric reactions. For leading references, see: (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180. (b) Mannich-type reaction: Kobayashi, S.; Kobayashi, J.; Ishitani, H.; Ueno, M. Chem.-Eur. J. 2002, 8, 4185. (c) Allylation using allyltributyltins: Gastner, T.; Ishitani, H.; Kobayashi, S. Angew. Chem. Int. Ed. 2001, 40, 1896.
16. We have successfully utilized 2-aminophenols-derived imines for chiral zirconium-catalyzed asymmetric reactions. For leading references, see: (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180. (b) Mannich-type reaction: Kobayashi, S.; Kobayashi, J.; Ishitani, H.; Ueno, M. Chem.-Eur. J. 2002, 8, 4185. (c) Allylation using allyltributyltins: Gastner, T.; Ishitani, H.; Kobayashi, S. Angew. Chem. Int. Ed. 2001, 40, 1896.
17. 4, filtered, and purified by preparative TLC (hexane/ethyl acetate, 6:1) to give adduct 5 or 7.
18. Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409.
19. Phenyliodonium dicarboxylate-mediated intra- and intermolecular carbon-carbon bond-forming reactions of phenols with alkenes were reported, see: (a) Swenton, J. S.; Carpenter, K.; Chen, Y.; Kerns, M. L.; Morrow, G. W. J. Org. Chem. 1993, 58, 3308. (b) Quideau, S.; Pouységu, L.; Oxoby, M.; Looney, M. A. Tetrahedron 2001, 57, 319.
20. Phenyliodonium dicarboxylate-mediated intra- and intermolecular carbon-carbon bond-forming reactions of phenols with alkenes were reported, see: (a) Swenton, J. S.; Carpenter, K.; Chen, Y.; Kerns, M. L.; Morrow, G. W. J. Org. Chem. 1993, 58, 3308. (b) Quideau, S.; Pouységu, L.; Oxoby, M.; Looney, M. A. Tetrahedron 2001, 57, 319.
21. Products 8 were prepared from crotylation of 2-amino-p-cresol/benzaldehyde-imine under the conditions similar to crotylation of 3a (Scheme 1). The reactions with (E)- and (Z)-6 at r.t. for 5 h provided syn-8 (74% yield, 86% syn) and anti-8 (76% yield, ≥99% anti), respectively.
22. Hoffmann, R. W.; Endesfelder, A. Liebigs Ann. Chem. 1987, 215.