Cycloadditions of chiral carbonyl ylides with imine dipolarophiles as a route to enantiomerically pure α-amino-β-hydroxy acids

Tetrahedron Asymmetry

Volumn 20, Issue 6-8, 2009, Pages 723-725

  Gan, Yu ^a   Harwood, Laurence M ^a   Richards, Simon C ^a   Smith, Ian E D ^b   Vinader, Victoria ^b  

^a UNIVERSITY OF READING   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBONYL DERIVATIVE; HYDROXYACID; IMINE; MORPHOLINE DERIVATIVE;

ARTICLE; CHIRALITY; CONVALESCENCE; CYCLOADDITION; DIASTEREOISOMER; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL;

EID: 65549096014     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.02.029     Document Type: Article

References (19)

1. Katsuki T., and Sharpless K.B. J. Am. Chem. Soc. 102 (1980) 5974
2. Denis J.N., Correa A., and Greene A.E. J. Org. Chem. 55 (1990) 1957
3. Torssell S., Kienle M., and Somfai P. Angew. Chem., Int. Ed. 44 (2005) 3096
4. Denis J.N., Correa A., and Greene A.E. J. Org. Chem. 56 (1991) 6939
5. Umezawa H., Aoyagi T., Suda H., Hamada M., and Takeuchi T. J. Antibiot. 29 (1976) 97
6. Rich D.H. J. Med. Chem. 28 (1985) 263
7. Moon S.S., Chen J.L., Moore R.E., and Patterson G.M.L. J. Org. Chem. 57 (1992) 1097
8. Juaristi E. Enantioselective Synthesis of β-Amino Acids (1997), John Wiley & Sons, New York
9. Nicolaou K.C., Dai W.M., and Guy R.K. Angew. Chem., Int. Ed. 33 (1994) 15
10. Crown J., and O'Leary M. Lancet 355 (2000) 1176
11. Angell R., Fengler-Veith M., Finch H., Harwood L.M., and Tucker T.T. Tetrahedron Lett. 38 (1997) 4517
12. Drew M.G.B., Fengler-Veith M., Harwood L.M., and Jahans A.W. Tetrahedron Lett. 38 (1997) 4521
13. Sato M., Kanuma N., and Kato T. Chem. Pharm. Bull. 30 (1982) 1315
14. Green G.M., Peet N.P., and Metz W.A. J. Org. Chem. 66 (2001) 2509
15. Regitz M. Angew. Chem., Int. Ed. Engl. 6 (1967) 733
16. 20 = - 51.9
17. 2 using shelx97. Final R = 0.0417, weighted R = 0.1327. CCDC 717010 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
18. Evans D.A., Britton T.C., and Ellman J.A. Tetrahedron Lett. 28 (1987) 6141
19. Borah J.C., Boruwa J., and Barua N.C. Curr. Org. Chem. 4 (2007) 175