Enantioselective synthesis of β-hydroxy amines and aziridines using asymmetric transfer hydrogenation of α-amido ketones

Tetrahedron Asymmetry

Volumn 11, Issue 16, 2000, Pages 3257-3261

  Kawamoto, Aparecida ^a   Wills, Martin ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0034714104     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00310-4     Document Type: Article

References (19)

1. (a) For a comprehensive survey of methods of aziridine synthesis from double bonds, including a discussion of cyclisations of β-amino alcohols, see; Kemp, J. E. G. In Comprehensive Organic Synthesis; Academic Press: New York, 1991; Vol. 7, Chapter 3.5, pp. 470-483.
2. (b) Atkinson, R. S.; Kelly, B. J. J. Chem. Soc., Chem. Commun. 1987, 1362.
3. (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 113, 6744.
4. (b) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
5. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. J. Am. Chem. Soc. 1993, 115, 5328.
6. (a) Kenny, J. A.; Palmer, M. J.; Smith, A. R. C.; Walsgrove, T.; Wills, M. Synlett 1999, 1615.
7. (b) Palmer, M. J.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226.
8. (c) Wills, M.; Palmer, M. J.; Smith, A. R. C.; Kenny, J. A.; Walsgrove, T. Molecules 2000, 5, 1-15.
9. (d) Kenny, J. A.; Versluis, K.; Heck, A. J. R.; Walsgrove, T.; Wills, M. Chem. Commun. 2000, 99-100.
10. (e) Kenny, J. A.; Walsgrove, T.; Wills, M., unpublished result.
11. D=+3.5 (c=1, EtOH), HPLC (hexane:ethanol:diethylamine 95:4.9:0.1) 41.62 (R), 22.48 (S).
12. (a) Wessig, P.; Schwarz, J. Synlett 1997, 893.
13. (b) Effenberger, F.; Stelzer, U. Tetrahedron: Asymmetry 1995, 6, 283.
14. (a) General reference: Mitsunobu, O. In Comprehensive Organic Synthesis; Academic Press: New York, 1991; Vol. 6, Chapter 1.3, pp. 93-98.
15. (b) Specific to epoxides: Pfister, J. R. Synthesis 1984, 969.
16. 2).
17. D=+39.2 (c=1, DCM) for the (S) enantiomer (Ref. 6a). In this case, the expected aziridine configuration, (R), matches that found by comparison with the literature.
18. Kitaori K., Furukawa Y., Yoshimoto H., Otera J. Tetrahedron Lett. 39:1998;3173.
19. Ketone 13 was conveniently prepared by the epoxidation of N-tBoc-allylamine, followed by ring-opening with sodium phenoxide and oxidation of the alcohol (80% overall yield). An alternative method, avoiding an alcohol oxidation step but resulting in a slightly lower yield, involves sequential reaction of 2-bromomethylallylbromide with phenol and sodium azide, reduction of azide and amine protection, followed by ozonolysis of the alkene.