Preparation of both diastereomers of homoallylic amines by allylmetalation of methyl N-benzylidene-(S)-valinate

Synlett

Volumn , Issue 4, 1998, Pages 367-368

  El Shehawy, Ashraf A ^a   Omara, Mahmoud A ^b   Ito, Koichi ^a   Itsuno, Shinichi ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b TANTA UNIVERSITY   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002909343     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1681     Document Type: Article

References (16)

1. (a) Enders, D.; Reinhold, U. Tetrahedron Asymmetry, 1997, 8, 1895.
2. (b) Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun., 1996, 999.
3. (a) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem. Int. Ed. Engl., 1997, 36, 109.
4. (b) El-Shehawy, A. A.; Abdelaal, M. Y.; Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron Asymmetry, 1997, 8, 1731.
5. (c) Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron Asymmetry, 1995, 6, 1531.
6. (d) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc., 1996, 118, 8489.
7. (a) Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun., 1996, 367.
8. (b) Enders, D.; Schankat, J.; Klatt, M. Synlett, 1994, 795.
9. Tanaka, H.; Inoue, K.; Pokorski, U.; Taniguchi, M.; Torii, S. Tetrahedron Lett. 1990, 31, 3023.
10. (a) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem., 1994, 59, 7766.
11. (b) Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc., Chem. Commun., 1993, 1542.
12. (c) Bocoum, A.; Boga, C.; Savoia, D.; Umani-Ronchi, A. Tetrahedron Lett., 1991, 32, 1367.
13. 2O (56 mg, 0.15 mmol) and a solution of 1 (0.219 g, 1 mmol) and methallyl bromide (0.162 g, 1.2 mmol) in THF (3 ml). The reaction mixture was stirred for 24 h at 25 °C and then quenched with 10% aq NaOH (5 ml). After usual work-up, 2b was isolated with satisfactory purity.
14. 5a.
15. 3·Et2O (0.12 ml, 1 mmol) and a solution of 1 (0.219 g, 1 mmol) in THF (3 ml) were added. The mixture was stirred for further 30 min at room temperature. After usual work-up, 2a was isolated with satisfactory purity.
16. Two isomers were separated by flash column chromatography using hexane/ethyl acetate (4:1) as eluent.