Simple Aziridino Alcohols as Chiral Ligands. Enantioselective Additions of Diethylzinc to N-Diphenylphosphinoylimines

Synlett

Volumn 1996, Issue 8, 1996, Pages 727-728

  Andersson, Pher G ^a   Guijarro, David ^a   Tanner, David ^b  

^a UPPSALA UNIVERSITY   (Sweden)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001238773     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5529     Document Type: Article

References (13)

1. See, e.g., Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
2. Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097.
3. Review: Tanner, D. Angew. Chem. Int. Ed. Engl. 1994, 33, 599.
4. Tanner, D.; Harden, A.; Johansson, F.; Wyatt, P.; Andersson, P. G. Acta Chem. Scand. 1996, 50, 361.
5. a) Shaw, K. J.; Luly, J. R.; Rapoport, H.; J. Org. Chem. 1985, 50, 4515.
6. b) Schwan, A. L.; Refvik, M. D. Tetrahedron Lett. 1993, 34, 4901.
7. c) Capeller, R. V.; Griot, R.; Häring, M.; Wagner-Jauregg, T. Helv. Chim. Acta 1957, 40, 1652.
8. Elliott, D. F. J. Chem. Soc. 1950, 62.
9. For a discussion, see: Jennings, W. B.; Boyd, D. R. in Cyclic Organonitrogen Stereodynamics (Eds.: Lambert, J.; Takeuchi, Y.), VCH, New York, 1992.
10. Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561.
11. 4. Solvents were evaporated and the resulting residue was purified by flash chromatography (silica gel, pentane/chloroform/methanol: 80/20/1). The resulting solid was analysed by HPLC, using a chiral column (ChiralCel OD-H), 254 nm UV detector, 5% i-PrOH in hexane as eluent and a flow rate of 0.5 ml/min. The retention times were 24.7 min for the (R)-isomer and 36.9 min for the (S)-isomer.
12. 4. Evaporation of the solvent gave the pure 1-phenylpropylamine.
13. The reaction was stirred for 7 days at room temperature and it did not reach completion.