Protic solvent-promoted neutral allylation of aldehydes and ketones with 1,8-bis(allylstannyl)naphthalenes

Synlett

Volumn , Issue 4, 1998, Pages 377-378

  Asao, Naoki ^a   Abe, Noriko ^a   Tan, Zheng ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003162888     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1679     Document Type: Article

References (12)

1. Asao, N.; Liu, P.; Maruoka, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2507.
2. Reviews on the reactivity of allylstannane: a) Yamamoto, Y. Aldrichim. Acta 1987, 20, 45;
3. b) Yamamoto, Y. Acc. Chem. Res. 1987, 20, 243;
4. c) Hull, C.; Mortlock, S. V.; Thomas, E. J. Tetrahedron 1989, 45, 1007;
5. d) Nishigaichi, Y.; Takuwa, A.; Nanita, Y.; Maruyama, K. Tetrahedron ibid. 1993, 49, 7395.
6. a) Cokley, T. M.; Marshall, R. L.; McCluskey, A.; Young, D. J. Tetrahedron Lett. 1996, 37, 1905;
7. b) Cokley, T. M.; Harvey, P. J.; Marshall, R. L.; McCluskey, A.; Young, D. J. J. Org. Chem. 1997, 62, 1961.
8. Attempted allylation of benzaldehyde with 1-(allyldibutylstannyl)naphthalene in place of 3 gave similar results.
9. 2 = H) (61 mg, 82% yield) as a colorless oil.
10. The similar eight-membered transition state was suggested in the reaction of tetraallyltin with aldehydes in methanol: See ref. 3.
11. Brønsted acid catalyzed allylations: a) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 1053;
12. b) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313.