Barbier-type allylation of chiral α-Aminoaldehydes: Dependence of the stereochemical outcome on metal and allylic halide

Tetrahedron

Volumn 53, Issue 8, 1997, Pages 2823-2834

  Rübsam, Frank ^a   Seck, Stephan ^a   Giannis, Athanassios ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINOALCOHOL;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031584939     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00050-1     Document Type: Article

References (32)

1. 1. J. Jurczak, A. Golebiowski, Chem. Rev. 1989, 89, 149-164; M.T. Reetz, Angew. Chem. 1991, 103, 1559-1573, Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1545.
2. 1. J. Jurczak, A. Golebiowski, Chem. Rev. 1989, 89, 149-164; M.T. Reetz, Angew. Chem. 1991, 103, 1559-1573, Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1545.
3. 1. J. Jurczak, A. Golebiowski, Chem. Rev. 1989, 89, 149-164; M.T. Reetz, Angew. Chem. 1991, 103, 1559-1573, Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1545.
4. 2. M.T. Reetz, M.W. Drewes, A. Schmitz, Angew. Chem. 1987, 99, 1186-1188, Angew. Chem. Int. Ed. Engl. 1987, 26, 1141-1143; W.D. Lubell, H.J. Rapoport, J. Am. Chem. Soc. 1987, 109, 236-239; P. Garner, J.M. Park, J. Org. Chem. 1987, 52, 2361-2364.
5. 2. M.T. Reetz, M.W. Drewes, A. Schmitz, Angew. Chem. 1987, 99, 1186-1188, Angew. Chem. Int. Ed. Engl. 1987, 26, 1141-1143; W.D. Lubell, H.J. Rapoport, J. Am. Chem. Soc. 1987, 109, 236-239; P. Garner, J.M. Park, J. Org. Chem. 1987, 52, 2361-2364.
6. 2. M.T. Reetz, M.W. Drewes, A. Schmitz, Angew. Chem. 1987, 99, 1186-1188, Angew. Chem. Int. Ed. Engl. 1987, 26, 1141-1143; W.D. Lubell, H.J. Rapoport, J. Am. Chem. Soc. 1987, 109, 236-239; P. Garner, J.M. Park, J. Org. Chem. 1987, 52, 2361-2364.
7. 2. M.T. Reetz, M.W. Drewes, A. Schmitz, Angew. Chem. 1987, 99, 1186-1188, Angew. Chem. Int. Ed. Engl. 1987, 26, 1141-1143; W.D. Lubell, H.J. Rapoport, J. Am. Chem. Soc. 1987, 109, 236-239; P. Garner, J.M. Park, J. Org. Chem. 1987, 52, 2361-2364.
8. 3. A. Giannis, T. Henk, Tetrahedron Lett. 1990, 31, 1253-1256.
9. 4. T. Kolter, A. Klein, A. Giannis, Angew. Chem. 1992, 104, 1394-1395, Angew. Chem. Int. Ed. Engl. 1992, 31, 1391-1392.
10. 4. T. Kolter, A. Klein, A. Giannis, Angew. Chem. 1992, 104, 1394-1395, Angew. Chem. Int. Ed. Engl. 1992, 31, 1391-1392.
11. 5. T. Kolter, C. Dahl, A. Giannis, Liebigs Ann. 1995, 625-629.
12. 6. F. D Ániello, M. Taddei, J. Org. Chem. 1992, 57, 5247-5250; P. Ciapetti, M. Taddei, P. Ulivi, Tetrahedron Lett. 1994, 35, 3183-3186.
13. 6. F. D Ániello, M. Taddei, J. Org. Chem. 1992, 57, 5247-5250; P. Ciapetti, M. Taddei, P. Ulivi, Tetrahedron Lett. 1994, 35, 3183-3186.
14. 7. D.H. Rich, C.-Q. Sun, J.V.N.V. Prasad, A. Ahammadunny, M.V. Toth, G.R. Marshall, M. Clare, R.A. Mueller, K. Houseman, J. Med. Chem. 1991, 34, 1225-1228; A. Fässler, J. Rösel, M. Grütter, M. Tintelnot-Blomley, E. Alteri, G. Bold, M. Lang, BioMed. Chem. Lett. 1993, 3, 2837-2842.
15. 7. D.H. Rich, C.-Q. Sun, J.V.N.V. Prasad, A. Ahammadunny, M.V. Toth, G.R. Marshall, M. Clare, R.A. Mueller, K. Houseman, J. Med. Chem. 1991, 34, 1225-1228; A. Fässler, J. Rösel, M. Grütter, M. Tintelnot-Blomley, E. Alteri, G. Bold, M. Lang, BioMed. Chem. Lett. 1993, 3, 2837-2842.
16. 8. E.F. Kleinman, A.H. Fray, W.F. Holt, M.A.R. Kiron, W.R. Murphy, I.M. Purcell, R.L. Rosati, BioMed. Chem. Lett. 1994, 4, 589-592.
17. 9. J.A. Matson, C. Claridge, J.A. Bush, J. Titus, W.T. Bradner, T.W. Doyle, A.C. Horan, M. Palel, J. Antibiot. 1989, 42, 1547-1555.
18. 10. K.C. Nicolaou, C.W. Hummel, E.N. Pitsinos, M. Nakada, A.L. Smith, K. Shibayama, H. Saimoto, J. Am. Chem. Soc. 1992, 114, 10082-10084.
19. 11. V. Constantinou-Kokotou, G. Kokotos, M. Chrysayi-Tokousbalides, E.A. Couladouros, M.P. Georgiadis, Liebigs Ann. Chem. 1994, 847-850.
20. 12. C.-J. Li, Tetrahedron 1996, 52, 5643-5668.
21. 13. Review: C. Blomberg, F.A. Hartog, Synthesis 1977, 18-30.
22. 14. C. Petrier, J. Einhorn, J.-L. Luche, Tetrahedron Lett. 1985, 26, 1449-1452.
23. 15. W. Schmid, G.M. Whitesides, J. Am. Chem. Soc. 1991, 113, 6674-6675.
24. 16. R.H. Prenner, W.H. Binder, W. Schmid, Liebigs Ann. Chem. 1994, 73-78.
25. 17. E. Kim, D.M. Gordon, W. Schmid, G.M. Whitesides, J. Org. Chem. 1993, 58, 5500-5507;
26. Allylation of N-Acetyl-Mannosamine proceeds only with indium: D.M. Gordon, G.M. Whitesides, J. Org. Chem. 1993, 58, 7937-7938.
27. 18. M. Chérest, H. Felkin, N. Prudent, Tetrahedron Lett. 1968, 2199-2204; N.T. Anh, Top. Curr. Chem. 1980, 88, 145-162.
28. 18. M. Chérest, H. Felkin, N. Prudent, Tetrahedron Lett. 1968, 2199-2204; N.T. Anh, Top. Curr. Chem. 1980, 88, 145-162.
29. 19. C. Einhorn, J.-L. Luche, J. Organometal. Chem. 1987, 322, 177-183.
30. 20. Hitherto, the use of secondary allylic halides in this reaction remained restricted to simple achiral aldehydes: S.R. Wilson, M.E. Guazzaroni, J. Org. Chem. 1989, 54, 3087-3091; T.A. Killinger, N.A. Boughton, T.A. Runge, J. Wolinski, J. Organomet. Chem. 1977, 124, 131-134.
31. 20. Hitherto, the use of secondary allylic halides in this reaction remained restricted to simple achiral aldehydes: S.R. Wilson, M.E. Guazzaroni, J. Org. Chem. 1989, 54, 3087-3091; T.A. Killinger, N.A. Boughton, T.A. Runge, J. Wolinski, J. Organomet. Chem. 1977, 124, 131-134.
32. 21. Review: Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.