A facile enantioselective synthesis of 2-(2-aminoethyl)allylsilanes, new synthons for piperidine synthesis

Tetrahedron Letters

Volumn 44, Issue 31, 2003, Pages 5785-5787

  Monfray, Jérémy ^a   Gelas Mialhe, Yvonne ^a   Gramain, Jean Claude ^a   Remuson, Roland ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

Allylsilane; Amine; Diastereoselectivity; Organocerium

Indexed keywords

PIPERIDINE; SILANE DERIVATIVE;

ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 0037632195     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01428-X     Document Type: Article

References (10)

1. (a) Strunz G.M., Findlay J.A. Brossi A. The Alkaloids. 26:1985;89 Academic Press, New York.
2. (b) Angle S.R., Breitenbucher J.G. Atta-ur-Rahman. Studies in Natural Products. 16:1995;453 Elsevier Science, Amsterdam.
3. (c) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc., Chem. Commun. 1998;633-640.
4. Cellier M., Gelas-Mialhe Y., Husson H.-P., Perrin B., Remuson R. Tetrahedron: Asymmetry. 11:2000;3913-3919.
5. Chalard P., Remuson R., Gelas-Mialhe Y., Gramain J.-C., Canet I. Tetrahedron Lett. 40:1999;1661-1664. and references cited therein.
6. Bardot V., Gelas-Mialhe Y., Gramain J.-C., Remuson R. Tetrahedron: Asymmetry. 8:1997;1111-1114.
7. Davies S.G., Ichihara O. Tetrahedron: Asymmetry. 2:1991;183-186.
8. 3): δ 142.6; 139.2; 129.8; 129.1; 128.7; 128.4; 127.4; 75.8; 56.2; 49.0; 48.9; 45.8; 34.9; 33.1; 18.7; 13.6; 1.1; 0.4.
9. 3): δ 75.6; 50.8; 45.2; 35.00; 32.7; 28.0; 0.9; 0.6.
10. 3): δ 145.3; 109.6; 49.4; 44.6; 26.5; 23.9, -0.4.