Stereochemical aspects in the asymmetric Michael addition of chiral imines to substituted electrophilic alkenes

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4361-4368

  Cavé, Christian ^a   Desmaële, Didier ^a   D'Angelo, Jean ^a   Riche, Claude ^a   Chiaroni, Angèle ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000396889     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960140k     Document Type: Article

References (18)

1. Review: Fuji, K. Chem. Rev. 1993, 93, 2037-2066.
2. Reviews: (a) d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459-505. (b) d'Angelo, J.; Cavé, C.; Desmaële, D.; Dumas, F. Trends in Organic Synthesis; Pandalai, S. G., Ed.; Trivandrum: India, 1993; Vol. 4, pp 555-615.
3. Reviews: (a) d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459-505. (b) d'Angelo, J.; Cavé, C.; Desmaële, D.; Dumas, F. Trends in Organic Synthesis; Pandalai, S. G., Ed.; Trivandrum: India, 1993; Vol. 4, pp 555-615.
4. Ambroise, L.; Desmaële, D.; Mahuteau, J.; d'Angelo, J. Tetrahedron Lett. 1994, 35, 9705-9708.
5. (a) Huffman, J. W.; Rowe, C. D.; Matthews, F. J. J. Org. Chem. 1982, 47, 1438-1445.
6. (b) Desmaële, D.; d'Angelo, J.; Bois, C. Tetrahedron: Asymmetry 1990, 1, 759-762.
7. 4 and therefore the reported stereochemistries do not necessarily reflect the geometrical arrangement of the reactants in the corresponding transition states.
8. Cavé, C.; Daley, V.; d'Angelo, J.; Guingant, A. Tetrahedron: Asymmetry 1995, 6, 79-82.
9. 6
10. Mekouar, K.; Ambroise, L.; Desmaële, D.; d'Angelo, J. Synlett 1995, Special Issue May, 529-532.
11. d'Angelo, J.; Guingant, A.; Riche, C.; Chiaroni, A. Tetrahedron Lett. 1988, 29, 2667-2670.
12. Barta, N. S.; Brode, A.; Stille, J. R. J. Am. Chem. Soc. 1994, 116, 6201-6206.
13. For the Michael-type reaction of 2-methyl(benzylimino)cyclohexane with maleic anhydride, see: Pfau, M.; Tomas, A.; Lim, S.; Revial, G. J. Org. Chem. 1995, 60, 1143-1147.
14. Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812.
15. Sevin, A.; Tortajada, J.; Pfau, M. J. Org. Chem. 1986, 51, 2671-2675.
16. Scheldrick, G. SHELSX86. Program for crystal structure determination: University of Göttingen: Germany, 1985.
17. Scheldrick, G. SHELSX76. Program for crystal structure determination: University of Cambridge: United Kingdom, 1976.
18. The authors have deposited atomic coordinates for (±)-16 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.