New chiral allylaminosilanes and their use in asymmetric Sakurai reactions

Tetrahedron Asymmetry

Volumn 9, Issue 17, 1998, Pages 2979-2981

  Bonini, B F ^a   Comes Franchini, M ^a   Fochi, M ^a   Mazzanti, G ^a   Ricci, A ^a   Varchi, G ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; SILANE DERIVATIVE;

ARTICLE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032483449     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00327-9     Document Type: Article

References (12)

1. Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 16, 1295-1298.
2. Chan, T. H.; Wang, D. Chem. Rev. 1992, 92, 995-1006.
3. Chan, T. H.; Wang, D. Tetrahedron Lett. 1989, 23, 3041-3044.
4. Denmark, S. E.; Henke, B. R.; Weber, E. J. Am. Chem. Soc. 1987, 109, 2512-2514.
5. Coppi, L.; Mordini, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 969-972.
6. Ito, Y.; Nakayo, K.; Tamao, K. Tetrahedron 1988, 44, 3997-4007.
7. Tamao, K.; Kanatani, R.; Kumada, M. Tetrahedron Lett. 1984, 25, 1913-1916.
8. 3N (Scheme 1) were used. (S)-(+)-2-Methoxymethyl pyrrolidine 1a has been prepared starting from L-proline according to Seebach, D.; Kalinowski, H. O. Helv. Chim. Acta 1977, 60, 300-325.
9. 3N (Scheme 1) were used. (S)-(+)-2-Methoxymethyl pyrrolidine 1a has been prepared starting from L-proline according to Seebach, D.; Kalinowski, H. O. Helv. Chim. Acta 1977, 60, 300-325.
10. +), 212, 186, 168, 128, 99, 70, 59
11. 6).
12. Riediker, M.; Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1989, 28, 494-495. All the enantiomeric excesses were confirmed by GC analysis of the corresponding trimethylsilyl ethers on a chiral capillary column (Megadex 5.25 m).