On indium(III) chloride-catalyzed aldol reactions of silyl enol ethers with aldehydes in water

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1579-1582

  Kobayashi, Shu ^a   Busujima, Tsuyoshi ^a   Nagayama, Satoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; INDIUM CHLORIDE; SILANE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; HYDROLYSIS;

EID: 0032546286     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00033-1     Document Type: Article

References (20)

1. (1) Kobayashi, S. Chem. Lett. 1991, 2187-2190; Kobayashi, S. Synlett 1994, 689-701.
2. (1) Kobayashi, S. Chem. Lett. 1991, 2187-2190; Kobayashi, S. Synlett 1994, 689-701.
3. (2) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625-1628; Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371-373; Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474; Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590-3596; Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2342-2344; Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1997, 959-960. Cf. Otto, S.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 2645-2648; Otto, S.; Bertoncin, F.; Engberts, J. B. F. N., J. Am. Chem. Soc. 1996, 118, 7702-7707.
4. (2) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625-1628; Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371-373; Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474; Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590-3596; Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2342-2344; Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1997, 959-960. Cf. Otto, S.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 2645-2648; Otto, S.; Bertoncin, F.; Engberts, J. B. F. N., J. Am. Chem. Soc. 1996, 118, 7702-7707.
5. (2) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625-1628; Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371-373; Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474; Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590-3596; Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2342-2344; Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1997, 959-960. Cf. Otto, S.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 2645-2648; Otto, S.; Bertoncin, F.; Engberts, J. B. F. N., J. Am. Chem. Soc. 1996, 118, 7702-7707.
6. (2) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625-1628; Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371-373; Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474; Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590-3596; Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2342-2344; Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1997, 959-960. Cf. Otto, S.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 2645-2648; Otto, S.; Bertoncin, F.; Engberts, J. B. F. N., J. Am. Chem. Soc. 1996, 118, 7702-7707.
7. (2) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625-1628; Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371-373; Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474; Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590-3596; Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2342-2344; Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1997, 959-960. Cf. Otto, S.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 2645-2648; Otto, S.; Bertoncin, F.; Engberts, J. B. F. N., J. Am. Chem. Soc. 1996, 118, 7702-7707.
8. (2) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625-1628; Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371-373; Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474; Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590-3596; Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2342-2344; Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1997, 959-960. Cf. Otto, S.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 2645-2648; Otto, S.; Bertoncin, F.; Engberts, J. B. F. N., J. Am. Chem. Soc. 1996, 118, 7702-7707.
9. (2) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625-1628; Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371-373; Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474; Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590-3596; Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2342-2344; Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1997, 959-960. Cf. Otto, S.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 2645-2648; Otto, S.; Bertoncin, F.; Engberts, J. B. F. N., J. Am. Chem. Soc. 1996, 118, 7702-7707.
10. (2) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625-1628; Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371-373; Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474; Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590-3596; Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2342-2344; Kobayashi, S.; Nagayama, S.; Busujima, T. Chem. Lett. 1997, 959-960. Cf. Otto, S.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 2645-2648; Otto, S.; Bertoncin, F.; Engberts, J. B. F. N., J. Am. Chem. Soc. 1996, 118, 7702-7707.
11. (3) Loh, T. P.; Pei, J.; Cao, G. Q. J. Chem. Soc., Chem. Commun. 1996, 1819.
12. (4) Loh, T. P.; Pei, J.; Koh, K. S. V.; Cao, G. Q.; Li, X. R. Tetrahedron Lett. 1997, 38, 3465-3468; 3993-3994 (Corrigendum).
13. 3 according to the procedure reported in Ref. 4.
14. 3
15. (7) Water-promoted aldol reactions of silyl enol ethers with aldehydes were reported. Lubineau, A. J. Org. Chem. 1986, 51, 2142; Lubineau, A.; Meyer, E. Tetrahedron 1988, 44, 6065.
16. (7) Water-promoted aldol reactions of silyl enol ethers with aldehydes were reported. Lubineau, A. J. Org. Chem. 1986, 51, 2142; Lubineau, A.; Meyer, E. Tetrahedron 1988, 44, 6065.
17. (8) In Corrigendum, the Singapore group also reported that the reaction proceeded under neat (solvent-free) conditions.
18. (9) As for the amounts of Lewis acids used, improvement of yields by reducing the amounts was not observed in other cases (Cf. Table 1).
19. (10) Kobayashi, S.; Wakabayashi, T.; Nagayama, S.; Oyamada, H. Tetrahedron Lett. 1997, 38, 4559-4562.
20. (11) Less than 20% yields were observed without a surfactant in water.