Conjugate allylation to α,β-unsaturated aldehydes with amphiphilic alkylation system, ATPH/allylcerium reagents

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3947-3950

  Ooi, Takashi ^a   Miura, Tomoya ^a   Kondo, Yuichiro ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMPHOPHILE; REAGENT;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; SYNTHESIS;

EID: 0030992587     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00786-7     Document Type: Article

References (15)

1. Ooi, T.; Kondo, Y.; Maruoka, K. Angew. Chem. Int. Ed. Engl., in press.
2. The interaction of Li-F: (a) von Eikema Hommes, N. J. R.; Schleyer, P. v. R. Angew. Chem. Int. Ed.Engl. 1992, 31, 755.
3. (b) Saa, J. M.; Deya, P. M.; Suner, G. A.; Frontera, A. J. Am. Chem. Soc. 1992, 114, 9093. For details, see: Yamazaki, T.; Kitazume, T. J. Synth. Org. Chem. Jpn. 1996, 54, 665.
4. (b) Saa, J. M.; Deya, P. M.; Suner, G. A.; Frontera, A. J. Am. Chem. Soc. 1992, 114, 9093. For details, see: Yamazaki, T.; Kitazume, T. J. Synth. Org. Chem. Jpn. 1996, 54, 665.
5. (a) Maruoka, K.; Imoto, H.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 4131.
6. (b) Maruoka, K.; Shimada, I.; Imoto, H.; Yamamoto, H. Synlett 1994, 519.
7. (c) Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 9091.
8. (d) Saito, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 2928.
9. 1 or an allylcerium reagent (1,4-/1,2-adducts = 28:72). This result gave us an implication that an allylcerium might be a suitable reagent to realize the amphiphilic allylation of α,β-unsaturated aldehydes with ATPH.
10. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392. See also: Imamoto, T. Lanthanides in Organic Synthesis, Academic Press: London, 1994 and the references cited therein.
11. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392. See also: Imamoto, T. Lanthanides in Organic Synthesis, Academic Press: London, 1994 and the references cited therein.
12. 3 and allyllithium gave comparable reactivity and selectivity in the conjugate allylation reaction with ATPH (94% yield; 1,4-/1,2-adducts = 84 : 16).
13. 2O seems to be appropriate under our optimized conditions. See: Reuter, G.; Fink, H.; Seifert, H. J. Z. anorg. allg. Chem. 1994, 620, 665.
14. Attempted reaction of cinnamaldehyde/ATPH complex with 0.5 equiv of diallylcerium reagent resulted in lower selectivity and chemical yield (54%; 1,4/1,2-adducts = 69 : 31).
15. Guo, B.-S.; Doubleday, W.; Cohen, T. J. Am. Chem. Soc. 1987, 109, 4710.