An asymmetric synthesis of N-protected β-amino aldehydes and β-amino ketones

Synlett

Volumn 1995, Issue 7, 1995, Pages 700-702

  Davies, Stephen G ^a   McCarthy, Tom D ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

conjugate addition; homochiral; stereoselective; amino aldehydes; amino ketones

Indexed keywords

EID: 33846093623     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5059     Document Type: Article

References (28)

1. Dondoni, A.; Perrone, D. Synthesis, 1993, 1162.
2. Marko, I.E.; Chesney, A. Synth. Commun., 1990, 3167.
3. Mark, I.E.; Chesney, A. SynLett, 1992, 275.
4. Barluenga, J.; Viado, A.L.; Aguilar, E.; Fustero, S.; Olano, B. J. Org. Chem., 1993, 58, 5972
5. Palomo, C; Aizpurua, J.M.; Garcia, J.M.; Iturburu, M.; Odriozola, J.M. 7. Org. Chem., 1994, 59, 5184.
6. Baldwin, J.E.; Adlington, R.M.; Godfrey, C.R.A.; Gollins, D.W.; Smith, M.L.; Russel, A.T. SynLett, 1993, 51.
7. Nahm, S.; Weinreb, S.M. Tetrahedron Lett., 1981, 22, 3815.
8. O'Neill, B.T. In Comprehensive Organic Synthesis; Trost, B.M. and Fleming, I., Ed.; Pergamon Press, 1991, Vol 1, p. 399.
9. Sibi, M.P. Org. Prep. Proc. Int., 1993, 25, 15.
10. Evans, D.A.; Gauchet-Prunet, J.A. J. Org. Chem., 1993, 58, 2446.
11. Rodriques, K.E. Tetrahedron Lett., 1991, 32, 1275.
12. Kinas, R.; Pankiewicz, K.; Stec, W.J.; Farmer, P.B.; Foster, A.B.; Jarman, M.; J. Org. Chem., 1977, 42, 1650.
13. Furukawa, T.; Okawara, T.; Terawaki, Y. Chem. Pharm. Bull, 1977, 25, 1319.
14. Davies, S.G.; Ichihara, O. Tetrahedron Asymmetry, 1991, 2, 183.
15. Davies, S.G.; Ichihara, O.; Walters, I.A.S. J. Chem. Soc, Perkin Trans. 1, 1994, 1141.
16. Davies, S.G.; Walters, I.A.S. 7. Chem. Soc, Perkin Trans. 1, 1994, 1129.
17. Bunnage, M.E.; Chernega, A.N.; Davies, S.G.; Goodwin, C.J. 7. Chem. Soc, Perkin Trans. 1, 1994, 2373.
18. Costello, J.F.; Davies, S.G.; Ichihara, O. Tetrahedron Asymmetry, 1994, 5, 1999.
19. Davies, S.G.; Edwards, A.J.; Walters, I.A.S. Reel. Trav. Chim. Pays-Bas, 1995, in press.
20. The direct addition of lithium (S)-(oc-methylbenzyl)benzylamide to non-enolizable apVunsaturated ketones (eg chalcone) led to no addition product being isolated. Davies, S.G.; Ichihara, O. unpublished results.
21. Other N-acyl-O-alkyl hydroxylamines, which lack a P-amino group, are unstable to normal alkylation conditions (e.g. NaHMDS, RX,-78°C). Davies, S.G.; Hepworth, D. unpublished results.
22. Graham, S.L.; Scholz, H. J. Org. Chem., 1991, 56, 4260.
23. Keck, G.E.; McHardy, S.F.; Murray, J.A. Tetrahedron Lett, 1993, 34, 6215.
24. The lH n.m.r. spectrum at ambient temperature in CDCI3 was very broad due to amide bond rotomers.
25. Determined from the integration of the N-methyl or N-methoxy singlets. A 1:1 mixture of 4a and 5a was prepared by N-benzylation (BnBr, Na2C03, DCM/H2O) of 2 and 3.
26. Braun, M.; Waldmuller, D. Synthesis, 1989, 856.
27. Evans, D.A.; Kaldor, S.W.; Jones, T.K.; Clardy, J.; Stout, T.J. J. Am. Chem. Soc., 1990, 112, 7000.
28. The Wittig reaction of p-amino aldehydes and the application of the derived homochiral 8-amino-ccP-unsaturated esters and amides in the synthesis of stereodefined 1, 3-polyamines will be described in due course.