Asymmetric alkylidenecyclopropanes from the regioselective reduction of π 1,1-dimethyleneallyl palladium complexes

Tetrahedron Asymmetry

Volumn 8, Issue 7, 1997, Pages 1005-1009

  Chevtchouk, Timour ^a   Ollivier, Jean ^a   Salaün, Jacques ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYCLOPROPANE DERIVATIVE;

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

EID: 0030985549     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00076-1     Document Type: Article

References (47)

1. Small Ring Compounds in Organic Synthesis I-IV, de Meijere, A., Ed., Top. Curr. Chem. 1986, vol. 133; 1988, vol. 144; 1990, vol. 155.
2. Small Ring Compounds in Organic Synthesis I-IV, de Meijere, A., Ed., Top. Curr. Chem. 1986, vol. 133; 1987, vol. 135; 1987, vol. 135; 1990, vol. 155.
3. Small Ring Compounds in Organic Synthesis I-IV, de Meijere, A., Ed., Top. Curr. Chem. 1986, vol. 133; 1987, vol. 135; 1988, vol. 144; 1988, vol. 144;
4. Small Ring Compounds in Organic Synthesis I-IV, de Meijere, A., Ed., Top. Curr. Chem. 1986, vol. 133; 1987, vol. 135; 1988, vol. 144; 1990, vol. 155. 1990, vol. 155.
5. Salaün, J. Rearrangements Involving the Cyclopropyl Group, Rappoport, Z., Ed., The Chemistry of the Cyclopropyl Group Wiley, New York 1987, p. 809.
6. Salaün, J.; Karkour, B. Tetrahedron Lett. 1987, 28, 4669; Salaün, J.; Karkour, B.; Ollivier, J. Tetrahedron 1989, 45, 3151; Salaün, J. Chem. Rev. 1989, 89, 1247; Russ. J. Org. Chem. in press.
7. Salaün, J.; Karkour, B. Tetrahedron Lett. 1987, 28, 4669; Salaün, J.; Karkour, B.; Ollivier, J. Tetrahedron 1989, 45, 3151; Salaün, J. Chem. Rev. 1989, 89, 1247; Russ. J. Org. Chem. in press.
8. Salaün, J.; Karkour, B. Tetrahedron Lett. 1987, 28, 4669; Salaün, J.; Karkour, B.; Ollivier, J. Tetrahedron 1989, 45, 3151; Salaün, J. Chem. Rev. 1989, 89, 1247; Russ. J. Org. Chem. in press.
9. Salaün, J.; Karkour, B. Tetrahedron Lett. 1987, 28, 4669; Salaün, J.; Karkour, B.; Ollivier, J. Tetrahedron 1989, 45, 3151; Salaün, J. Chem. Rev. 1989, 89, 1247; Russ. J. Org. Chem. in press.
10. De Meijere, A.; Wessjohann, L. Synlett 1990, 20.
11. For a review on Cyclopropenes and Methylenecyclopropanes as Multifunctional Reagents in Transition Metal Catalyzed Reactions see Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77.
12. For a review on Cycloadditions onto Methylene-and Alkylidenecyclopropane Derivatives see Goti, A.; Cordero, F. M.; Brandi, A. Top. Curr. Chem. 1996, 178, 2.
13. Donaldson, W. A.; Wang, J.; Cepa, V. G.; Suson, J. D. J. Org. Chem. 1989, 54, 6056.
14. Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1988, 44, 5809; Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1988, 44, 5809.
15. Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1988, 44, 5809; Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1988, 44, 5809.
16. Lewis, R. T.; Motherwell, W. B.; Shipman, M. J. Chem. Soc., Chem. Commun. 1988, 948; Bapuji, S. A.; Motherwell, W. B.; Shipman, M. Tetrahedron Lett. 1989, 30, 7107; Motherwell, W. B.; Shipman, M. Tetrahedron Lett. 1991, 32, 1103; Yamago, S.; Nakamura, E. Tetrahedron 1989, 45, 3081.
17. Lewis, R. T.; Motherwell, W. B.; Shipman, M. J. Chem. Soc., Chem. Commun. 1988, 948; Bapuji, S. A.; Motherwell, W. B.; Shipman, M. Tetrahedron Lett. 1989, 30, 7107; Motherwell, W. B.; Shipman, M. Tetrahedron Lett. 1991, 32, 1103; Yamago, S.; Nakamura, E. Tetrahedron 1989, 45, 3081.
18. Lewis, R. T.; Motherwell, W. B.; Shipman, M. J. Chem. Soc., Chem. Commun. 1988, 948; Bapuji, S. A.; Motherwell, W. B.; Shipman, M. Tetrahedron Lett. 1989, 30, 7107; Motherwell, W. B.; Shipman, M. Tetrahedron Lett. 1991, 32, 1103; Yamago, S.; Nakamura, E. Tetrahedron 1989, 45, 3081.
19. Lewis, R. T.; Motherwell, W. B.; Shipman, M. J. Chem. Soc., Chem. Commun. 1988, 948; Bapuji, S. A.; Motherwell, W. B.; Shipman, M. Tetrahedron Lett. 1989, 30, 7107; Motherwell, W. B.; Shipman, M. Tetrahedron Lett. 1991, 32, 1103; Yamago, S.; Nakamura, E. Tetrahedron 1989, 45, 3081.
20. Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021; Stolle, A.; Becker, H.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1994, 35, 3517 and 3521.
21. Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021; Stolle, A.; Becker, H.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1994, 35, 3517 and 3521.
22. Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1; Cordero, F. M.; Brandi, A. Tetrahedron Lett. 1995, 36, 1343; Estieu, K.; Paugam, R.; Ollivier, J.; Salaün, J.; Cordero, D. M.; Goti, A.; Brandi, A. Angew. Chem. Int. Ed. in press.
23. Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1; Cordero, F. M.; Brandi, A. Tetrahedron Lett. 1995, 36, 1343; Estieu, K.; Paugam, R.; Ollivier, J.; Salaün, J.; Cordero, D. M.; Goti, A.; Brandi, A. Angew. Chem. Int. Ed. in press.
24. Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1; Cordero, F. M.; Brandi, A. Tetrahedron Lett. 1995, 36, 1343; Estieu, K.; Paugam, R.; Ollivier, J.; Salaün, J.; Cordero, D. M.; Goti, A.; Brandi, A. Angew. Chem. Int. Ed. in press.
25. Salaün, J.; Conia, J. M. J. Chem. Soc. Chem. Commun. 1971, 1579; Salaün, J.; Champion, J.; Conia, J. M. Org. Synth. 1977, 57, 36; Salaün, J. Top. Curr. Chem. 1988, 144, 1.
26. Salaün, J.; Conia, J. M. J. Chem. Soc. Chem. Commun. 1971, 1579; Salaün, J.; Champion, J.; Conia, J. M. Org. Synth. 1977, 57, 36; Salaün, J. Top. Curr. Chem. 1988, 144, 1.
27. Salaün, J.; Conia, J. M. J. Chem. Soc. Chem. Commun. 1971, 1579; Salaün, J.; Champion, J.; Conia, J. M. Org. Synth. 1977, 57, 36; Salaün, J. Top. Curr. Chem. 1988, 144, 1.
28. Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
29. Stolle, A.; Ollivier, J.; Piras, P. P.; Salaün, J.; de Meijere, A. J. Am. Chem. Soc. 1992, 114, 4051; Ollivier, J.; Piras, P. P.; Stolle, A.; Aufranc, P.; de Meijere, A.; Salaün, J. Tetrahedron Lett. 1992, 33, 3307; Ollivier, J.; Dorizon, Ph.; Piras, P. P.; de Meijere, A.; Salaün, J. Inorganica Chim. Acta 1994, 222, 37.
30. Stolle, A.; Ollivier, J.; Piras, P. P.; Salaün, J.; de Meijere, A. J. Am. Chem. Soc. 1992, 114, 4051; Ollivier, J.; Piras, P. P.; Stolle, A.; Aufranc, P.; de Meijere, A.; Salaün, J. Tetrahedron Lett. 1992, 33, 3307; Ollivier, J.; Dorizon, Ph.; Piras, P. P.; de Meijere, A.; Salaün, J. Inorganica Chim. Acta 1994, 222, 37.
31. Stolle, A.; Ollivier, J.; Piras, P. P.; Salaün, J.; de Meijere, A. J. Am. Chem. Soc. 1992, 114, 4051; Ollivier, J.; Piras, P. P.; Stolle, A.; Aufranc, P.; de Meijere, A.; Salaün, J. Tetrahedron Lett. 1992, 33, 3307; Ollivier, J.; Dorizon, Ph.; Piras, P. P.; de Meijere, A.; Salaün, J. Inorganica Chim. Acta 1994, 222, 37.
32. Guibé-Jampel, E.; Rousseau, G.; Salaün, J.J. Chem. Soc. Chem. Commun. 1987, 1081; Chetchouk, T.; Ollivier, J.; Salaün, J.; Merlet, D.; Courtieu, J. Tetrahedron: Asymmetry 1997, 8, 999.
33. Guibé-Jampel, E.; Rousseau, G.; Salaün, J.J. Chem. Soc. Chem. Commun. 1987, 1081; Chetchouk, T.; Ollivier, J.; Salaün, J.; Merlet, D.; Courtieu, J. Tetrahedron: Asymmetry 1997, 8, 999.
34. Fadel, A.; Salaün, J. Tetrahedron Lett. 1988, 29, 6257.
35. Salaün, J.; Almirantis, Y. Tetrahedron 1983, 39, 2421.
36. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A.; Prityckaja, T. S. Zh. Org. Khim. 1989, 25, 2244; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A. Synthesis 1991, 234; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345; Lee, J.; Kim, H.; Cha, J. K.; J. Am. Chem. Soc. 1995, 117, 9919
37. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A.; Prityckaja, T. S. Zh. Org. Khim. 1989, 25, 2244; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A. Synthesis 1991, 234; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345; Lee, J.; Kim, H.; Cha, J. K.; J. Am. Chem. Soc. 1995, 117, 9919
38. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A.; Prityckaja, T. S. Zh. Org. Khim. 1989, 25, 2244; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A. Synthesis 1991, 234; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345; Lee, J.; Kim, H.; Cha, J. K.; J. Am. Chem. Soc. 1995, 117, 9919
39. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A.; Prityckaja, T. S. Zh. Org. Khim. 1989, 25, 2244; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A. Synthesis 1991, 234; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345; Lee, J.; Kim, H.; Cha, J. K.; J. Am. Chem. Soc. 1995, 117, 9919
40. 2O) have failed, likely due to steric hindrance.
41. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2956; Tolman, C. A.; Seidel, W. C.; Gosser, L. W. J. Am. Chem. Soc. 1974, 96, 53.
42. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2956; Tolman, C. A.; Seidel, W. C.; Gosser, L. W. J. Am. Chem. Soc. 1974, 96, 53.
43. Tolman, C. A. Chem. Rev. 1977, 77, 313.
44. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 6785.
45. Wiberg, L. W. Angew. Chem. Int. Ed. Engl. 1986, 25, 312.
46. McGaffin, G.; Michalski, S.; Stolle, A.; Bräse, S.; Salaün, J.; de Meijere, A. Synlett 1992, 558.
47. +, 22.09), 95 (80.12), 81 (43.56), 67 (100), 55 (22.78), 53 (17.11), 41 (33.80).