The effects of the nature of catalyst and of the solvent on the stereoselectivity in amine-catalyzed asymmetric synthesis of substituted cyclohexa-1,3-dienes from prenal and monoesters of ylidenemalonic acids

Russian Chemical Bulletin

Volumn 47, Issue 1, 1998, Pages 82-90

  Serebryakov, E P ^a   Nigmatov, A G ^a   Shcherbakov, M A ^a   Struchkova, M I ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

3 methylbut 2 enal; Chiral dienamines; Chiral secondary amines and hydroxy amines; Monoalkyl ylidenemalonates; Net enantioselectivity

Indexed keywords

EID: 0032367820     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02495513     Document Type: Article

References (28)

1. D. Enders, O. Meyer, and G. Raabe, Synthesis, 1992, 1242; D. Enders, O. Meyer, G. Raabe, and J. Runsink, Synthesis, 1994, 66.
2. D. Enders, O. Meyer, and G. Raabe, Synthesis, 1992, 1242; D. Enders, O. Meyer, G. Raabe, and J. Runsink, Synthesis, 1994, 66.
3. J. Barluenga, F. Aznar, C. Valdés, and J. A. Martin, Anal. de Quim., 1993, 89, 115; J. Barluenga, F. Aznar, C. Valdés, J. A. Martin, S. Garcia-Grandez, and E. Martin, J. Am. Chem. Soc., 1993, 115, 4403.
4. J. Barluenga, F. Aznar, C. Valdés, and J. A. Martin, Anal. de Quim., 1993, 89, 115; J. Barluenga, F. Aznar, C. Valdés, J. A. Martin, S. Garcia-Grandez, and E. Martin, J. Am. Chem. Soc., 1993, 115, 4403.
5. A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1993, 233 [Russ. Chem. Bull., 1993, 42, 213 (Engl. Transl.)].
6. A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1993, 233 [Russ. Chem. Bull., 1993, 42, 213 (Engl. Transl.)].
7. A. G. Nigmatov, I. N. Kornilova, and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1996, 154 [Russ. Chem. Bull., 1996, 45, 144 (Engl. Transl.)].
8. A. G. Nigmatov, I. N. Kornilova, and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1996, 154 [Russ. Chem. Bull., 1996, 45, 144 (Engl. Transl.)].
9. A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1996, 663 [Russ. Chem. Bull., 1996, 45, 623 (Engl. Transl.)].
10. A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1996, 663 [Russ. Chem. Bull., 1996, 45, 623 (Engl. Transl.)].
11. Y. Izumi and A. Tai, Stereo-diferentiating Reactions, Kodansha, Tokyo, 1977, Ch. 3.
12. E. P. Serebryakov and A. G. Nigmatov, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 605 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 527 (Engl. Transl.)].
13. E. P. Serebryakov and A. G. Nigmatov, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 605 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 527 (Engl. Transl.)].
14. A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1079 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 961 (Engl. Transl.)].
15. A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1079 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 961 (Engl. Transl.)].
16. R. Tripathy, P. J. Carroll, and E. R. Thornton, J. Am. Chem. Soc., 1991, 113, 7630.
17. B. M. Trost and D. C. Lee, J Org. Chem., 1989, 54, 2271; J. C. Lopez and G. Lukas, Cycloaddition Reactions in Carbohydrate Chemistry. ACS Symp. Ser., 1992, Issue 494, 33.
18. B. M. Trost and D. C. Lee, J Org. Chem., 1989, 54, 2271; J. C. Lopez and G. Lukas, Cycloaddition Reactions in Carbohydrate Chemistry. ACS Symp. Ser., 1992, Issue 494, 33.
19. G. Opitz and W. Merz, Liebigs Ann. Chem., 1962, 652, 139; 158.
20. M. B. Erman, I. S. Aulchenko, L. A. Kheifits, V. G. Dulova, and M. E. Vol'pin, Tetrahedron Lett., 1976, 34, 2981.
21. D. Enders, P. Fey, and H. Kipphardt, Org. Prepn. Proc. Int., 1985, 17, 1.
22. R. G. Kostyanovsky, I. M. Gella, V. I. Markov, and Z. E. Samoilova, Tetrahedron, 1974, 30, 39.
23. G. F. Cooper, K. E. McCarthy, and M. G. Martin, Tetrahedron Lett., 1992, 33, 5895.
24. A. Orechoff and G. Menschikoff, Ber., 1931, 64, 266.
25. F. Toda, K. Tanaka, L. Nassimbeni, and M. Niven, Chem. Lett., 1988, 1371.
26. Fluka Chemika-Biochemika-Analytika, Fluka Chemie AG, CH-9471 Buchs (Switzerland), 1995/1996, 1022, Cat. No. 68622.
27. S. Hünig and H. Kahanek, Chem. Ber., 1957, 90, 238.
28. J. A. Riddick and W. B. Bunger, Techniques of Chemistry, 2, Organic Solvents, Wiley, New York, 1971.