Novel route to the synthesis of hydroxylated piperidine and pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 2109-2112

  Kadota, Isao ^a   Kawada, Miho ^a   Saya, Shioko ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029996420     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00205-5     Document Type: Article

References (15)

1. (a) Yamamoto, Y.; Yamada, J.; Kadota, I. Tetrahedron Lett. 1991, 32, 7069.
2. (b) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313.
3. (c) Yamamoto, Y.; Kadota, I. Main Group Met. Chem. 1994, 17, 269.
4. Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777.
5. (a) Ravelo, J. L.; Regueiro, A.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3389.
6. (b) Alvarez, E.; Díaz, M. T.; Pérez, R.; Ravelo, J. L.; Regueiro, A.; Vera, J. A.; Zurita, D.; Martín, J. D. J. Org. Chem. 1994, 59, 2848.
7. (c) Kadota, I.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1993, 1638.
8. (d) Yamamoto, Y.; Kadota, I. Bull. Soc. Chim. Belg. 1994, 103, 619.
9. (e) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953, and references sited therein.
10. Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull Soc. Chim. Belg. 1972, 81, 425.
11. (a) Schwartz, R. E.; Liesch, J.; Hensens, O.; Zitano, L.; Honeycutt, S.; Garrity, G.; Fromtling, R. A.; Onishi, J.; Monaghan, R. J. Antibiot. 1988, 41, 1774.
12. (b) Johnson, J. H.; Phillipson, D. W.; Kahle, A. D. J. Antibiot. 1989, 42, 1184.
13. In general, γ-aminoallylstannanes exhibit lower reactivity toward aldehydes than γ-alkoxyallylstannanes.
14. 3) δ 5.99 (ddd, J = 16.9, 10.5, 6.1 Hz, 1H), 5.36 (ddd, J = 10.5, 1.7, 1.7 Hz, 1H), 5.25 (ddd, J = 16.9, 1.7, 1.7 Hz, 1H), 4.87-4.78 (m, 1H), 3.96-3.84 (brd, J = 14.0 Hz, 1H), 3.83-3.70 (m, 1H), 2.77 (ddd, J = 12.9, 12.9, 3.4 Hz, 1H), 2.24-2.14 (brs, 1H), 1.46 (s, 9H), 1.76-1.25 (m, 4H).
15. 3) δ 5.80 (ddd, J = 17.0, 11.0, 6.0 Hz, 1H), 5.34 (brd, J = 11.0, Hz, 1H), 5.26 (brd, J = 17.0 Hz, 1H), 4.42-4.22 (m, 2H), 3.59-3.36 (m, 2H), 2.16-1.96 (m, 1H), 1.95-1.74 (m, IH), 1.44 (s, 9H).