Aldehydes vs Aldimines. Unprecedented Reactivity in Their Enolate Addition Reactions

Journal of Organic Chemistry

Volumn 62, Issue 2, 1997, Pages 232-233

  Kobayashi, Shu ^a   Nagayama, Satoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000050581     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962010h     Document Type: Article

References (27)

1. For example: Yamaguchi, M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1.11.
2. Very recently, Yamamoto et al. reported imine-selective allylation via a palladium-catalyzed allylstannane reaction. Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459; J. Am. Chem. Soc. 1996, 118, 6641.
3. Very recently, Yamamoto et al. reported imine-selective allylation via a palladium-catalyzed allylstannane reaction. Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459; J. Am. Chem. Soc. 1996, 118, 6641.
4. (a) Chan, T.-H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, Chapter 2.3.
5. (b) Mukaiyama, T.; Banno, K.; Narasaka, K. Chem. Lett. 1973, 357.
6. (c) Mukaiyama, T. Org. React. 1982, 28, 203.
7. (a) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, Chapter 4.1.
8. (b) Ojima I.; Inaba, S.; Yoshida, K. Tetrahedron Lett. 1977, 3643.
9. (c) Guanti, G.; Narisano, E.; Banfi, L. Tetrahedron Lett. 1987, 28, 4331.
10. (d) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397.
11. (e) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem Lett. 1990, 889.
12. (f) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141.
13. (g) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963.
14. Kobayashi, S. Synlett 1994, 689.
15. We have already found that lanthanide triflates are effective catalysts for the reactions of aldehydes or aldimines with silyl enolates. (a) Aldehyde: Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625. (b) Aldimine: Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
16. We have already found that lanthanide triflates are effective catalysts for the reactions of aldehydes or aldimines with silyl enolates. (a) Aldehyde: Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625. (b) Aldimine: Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
17. See also: (c) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809.
18. 4 was used.
19. (a) Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1.10.
20. (b) Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, 1995; Chapter 1.
21. 3 (1.0 equiv): δ 192.09.
22. 3 (1.0 equiv): δ 167.20.
23. Morrill, T. C. In Lanthanide Shift Reagents in Stereochemical Analysis; Morrill, T. C., Ed.; VCH: New York, 1986; Chapter 1.
24. 13 We have several contrary experimental results concerning this proposal. The present paper is thought to be one of them, and precise discussion will be reported in due course.
25. (a) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323. Cf.
26. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
27. (c) Denmark, S. E.; Chen, C.-T. Tetrahedron Lett. 1994, 35, 4327.