Asymmetric Synthesis of Substituted Functionalized Cis and Trans Vinylcyclopropanes via Palladium Catalyzed Reactions

Synlett

Volumn 1996, Issue 3, 1996, Pages 215-217

  Michelet, V ^a   Besnier, I ^a   Genet J P ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000241905     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5380     Document Type: Article

References (34)

1. Krief, A Stereocontrolled Organic Synthesis, Ed Trost B.M., Blackwell, 1994, 337. Salaün, J. Chem. Rev. 1989, 89, 1247. Doyle, M.P. Chem. Rev. 1986, 86, 919.
2. Krief, A Stereocontrolled Organic Synthesis, Ed Trost B.M., Blackwell, 1994, 337. Salaün, J. Chem. Rev. 1989, 89, 1247. Doyle, M.P. Chem. Rev. 1986, 86, 919.
3. Krief, A Stereocontrolled Organic Synthesis, Ed Trost B.M., Blackwell, 1994, 337. Salaün, J. Chem. Rev. 1989, 89, 1247. Doyle, M.P. Chem. Rev. 1986, 86, 919.
4. (a) Genêt, J.P.; Piau, F.; Ficini, J. Tetrahedron Lett. 1980, 21, 3183.
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12. (c) For a recent chiral development of this methodology, see: Kang, S-K.; Park, D-C.; Jeon, J-H.; Rho, H-S.; Yu, C-M. Tetrahedron Lett. 1994, 35, 2357.
13. (a) We have recently reported two general methods for the synthesis of a β-C-glycosyl aldehyde, precursor of A-ring. of ambruticine. Lasterra Sanchez, M.E.; Michelet, V.; Besnier, I.; Genêt, J.P. Synlett, 1994, 705.
14. (b) Our stategy also required a practical preparation of optically pure (R)-but-1-yn-3-ol in large scale We have developed an efficient preparation of the both enantiomers of this propargylic alcohol. Michelet, V.; Besnier, I., Tanier, S.; Touzin, A.M.; Genêt, J.P.; Demoute, J.P. Synthesis 1995, 165.
15. (c) For the first total synthesis see: Kende, A.S.; Mendoza, J.S.; Fujii, Y. Tetrahedron 1993, 49, 8015.
16. (d) For a partial synthesis see: Sinaÿ, P. Bio-Organic Heterocycles-Synthesis Mechanisms and Bioactivity, van der Plas H., Simonyi M., Aiderweireidt F.C., Lepoivre J.A. (eds); Elsevier, Amsterdam, 1986, 59 and references cited herein.
17. 2).
18. (a) The alkylation proceeds with via the more stable syn π allyl palladium intermediate. (Matrix Presented)
19. (b) For some reviews, see: (a) Godleski S.A. Comprehensive Organic Synthesis, Ed Trost, B.M., Pergammon Press, Oxford, 1991, 4, 585. (b) Trost, B.M., Angew. Chem. Int. Ed. Engl., 1989, 28, 1173. (c) Bäckvall, J.E. Acc. Chem. Res. 1983, 16, 335. (d) Tsuji, J. " Organic Synthesis with Palladium Compound " Springer Verlag, 1980, New York. (e) Trost, B.M. Acc. Chem. Res. 1980, 13, 385.
20. (b) For some reviews, see: (a) Godleski S.A. Comprehensive Organic Synthesis, Ed Trost, B.M., Pergammon Press, Oxford, 1991, 4, 585. (b) Trost, B.M., Angew. Chem. Int. Ed. Engl., 1989, 28, 1173. (c) Bäckvall, J.E. Acc. Chem. Res. 1983, 16, 335. (d) Tsuji, J. " Organic Synthesis with Palladium Compound " Springer Verlag, 1980, New York. (e) Trost, B.M. Acc. Chem. Res. 1980, 13, 385.
21. (b) For some reviews, see: (a) Godleski S.A. Comprehensive Organic Synthesis, Ed Trost, B.M., Pergammon Press, Oxford, 1991, 4, 585. (b) Trost, B.M., Angew. Chem. Int. Ed. Engl., 1989, 28, 1173. (c) Bäckvall, J.E. Acc. Chem. Res. 1983, 16, 335. (d) Tsuji, J. " Organic Synthesis with Palladium Compound " Springer Verlag, 1980, New York. (e) Trost, B.M. Acc. Chem. Res. 1980, 13, 385.
22. (b) For some reviews, see: (a) Godleski S.A. Comprehensive Organic Synthesis, Ed Trost, B.M., Pergammon Press, Oxford, 1991, 4, 585. (b) Trost, B.M., Angew. Chem. Int. Ed. Engl., 1989, 28, 1173. (c) Bäckvall, J.E. Acc. Chem. Res. 1983, 16, 335. (d) Tsuji, J. " Organic Synthesis with Palladium Compound " Springer Verlag, 1980, New York. (e) Trost, B.M. Acc. Chem. Res. 1980, 13, 385.
23. (b) For some reviews, see: (a) Godleski S.A. Comprehensive Organic Synthesis, Ed Trost, B.M., Pergammon Press, Oxford, 1991, 4, 585. (b) Trost, B.M., Angew. Chem. Int. Ed. Engl., 1989, 28, 1173. (c) Bäckvall, J.E. Acc. Chem. Res. 1983, 16, 335. (d) Tsuji, J. " Organic Synthesis with Palladium Compound " Springer Verlag, 1980, New York. (e) Trost, B.M. Acc. Chem. Res. 1980, 13, 385.
24. 4: C, 70.06; H, 6.61. Found: C, 70.04; H, 6.71.
25. Several examples on Pd(0) chirality transfer have been reported. Tsuji, J., Palladium Reagents, Ed Wiley J.and sons, New York, 1995.
26. (5) observed would be that the palladium (0) phosphine complex is attacking the π allyl-palladium intermediate. (Matrix Presented)
27. For some examples of asymmetric synthesis of cyclopropanes, see: (a) Nagasawa, T.; Handa, Y.; Onoguchi, S.; Ohba, S.; Suzuki, K. Synlett 1995, 739. (b) Charette, A.B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651. (c) Narjes, F.; Bolte, O.; Icheln, D.; König, W.A., Schaumann, E. J. Org. Chem. 1993, 58, 626. (d) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (e) Romo, D.; Meyers, A.I. J. Org. Chem. 1992, 57, 6265. (f) Lambs, L.; Singh, N.P., Biellmann, J.F. J. Org. Chem. 1992, 57, 66301, and references cited. (g) Hayashi T.; Yamamoto, A., Ito, Y. Tetrahedron Lett. 1988, 29, 669. (h) Monpert, A.; Martelli, J.; Grée, R., Carrié, R. Tetrahedron Lett. 1981, 22, 1961.
28. For some examples of asymmetric synthesis of cyclopropanes, see: (a) Nagasawa, T.; Handa, Y.; Onoguchi, S.; Ohba, S.; Suzuki, K. Synlett 1995, 739. (b) Charette, A.B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651. (c) Narjes, F.; Bolte, O.; Icheln, D.; König, W.A., Schaumann, E. J. Org. Chem. 1993, 58, 626. (d) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (e) Romo, D.; Meyers, A.I. J. Org. Chem. 1992, 57, 6265. (f) Lambs, L.; Singh, N.P., Biellmann, J.F. J. Org. Chem. 1992, 57, 66301, and references cited. (g) Hayashi T.; Yamamoto, A., Ito, Y. Tetrahedron Lett. 1988, 29, 669. (h) Monpert, A.; Martelli, J.; Grée, R., Carrié, R. Tetrahedron Lett. 1981, 22, 1961.
29. For some examples of asymmetric synthesis of cyclopropanes, see: (a) Nagasawa, T.; Handa, Y.; Onoguchi, S.; Ohba, S.; Suzuki, K. Synlett 1995, 739. (b) Charette, A.B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651. (c) Narjes, F.; Bolte, O.; Icheln, D.; König, W.A., Schaumann, E. J. Org. Chem. 1993, 58, 626. (d) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (e) Romo, D.; Meyers, A.I. J. Org. Chem. 1992, 57, 6265. (f) Lambs, L.; Singh, N.P., Biellmann, J.F. J. Org. Chem. 1992, 57, 66301, and references cited. (g) Hayashi T.; Yamamoto, A., Ito, Y. Tetrahedron Lett. 1988, 29, 669. (h) Monpert, A.; Martelli, J.; Grée, R., Carrié, R. Tetrahedron Lett. 1981, 22, 1961.
30. For some examples of asymmetric synthesis of cyclopropanes, see: (a) Nagasawa, T.; Handa, Y.; Onoguchi, S.; Ohba, S.; Suzuki, K. Synlett 1995, 739. (b) Charette, A.B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651. (c) Narjes, F.; Bolte, O.; Icheln, D.; König, W.A., Schaumann, E. J. Org. Chem. 1993, 58, 626. (d) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (e) Romo, D.; Meyers, A.I. J. Org. Chem. 1992, 57, 6265. (f) Lambs, L.; Singh, N.P., Biellmann, J.F. J. Org. Chem. 1992, 57, 66301, and references cited. (g) Hayashi T.; Yamamoto, A., Ito, Y. Tetrahedron Lett. 1988, 29, 669. (h) Monpert, A.; Martelli, J.; Grée, R., Carrié, R. Tetrahedron Lett. 1981, 22, 1961.
31. For some examples of asymmetric synthesis of cyclopropanes, see: (a) Nagasawa, T.; Handa, Y.; Onoguchi, S.; Ohba, S.; Suzuki, K. Synlett 1995, 739. (b) Charette, A.B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651. (c) Narjes, F.; Bolte, O.; Icheln, D.; König, W.A., Schaumann, E. J. Org. Chem. 1993, 58, 626. (d) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (e) Romo, D.; Meyers, A.I. J. Org. Chem. 1992, 57, 6265. (f) Lambs, L.; Singh, N.P., Biellmann, J.F. J. Org. Chem. 1992, 57, 66301, and references cited. (g) Hayashi T.; Yamamoto, A., Ito, Y. Tetrahedron Lett. 1988, 29, 669. (h) Monpert, A.; Martelli, J.; Grée, R., Carrié, R. Tetrahedron Lett. 1981, 22, 1961.
32. For some examples of asymmetric synthesis of cyclopropanes, see: (a) Nagasawa, T.; Handa, Y.; Onoguchi, S.; Ohba, S.; Suzuki, K. Synlett 1995, 739. (b) Charette, A.B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651. (c) Narjes, F.; Bolte, O.; Icheln, D.; König, W.A., Schaumann, E. J. Org. Chem. 1993, 58, 626. (d) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (e) Romo, D.; Meyers, A.I. J. Org. Chem. 1992, 57, 6265. (f) Lambs, L.; Singh, N.P., Biellmann, J.F. J. Org. Chem. 1992, 57, 66301, and references cited. (g) Hayashi T.; Yamamoto, A., Ito, Y. Tetrahedron Lett. 1988, 29, 669. (h) Monpert, A.; Martelli, J.; Grée, R., Carrié, R. Tetrahedron Lett. 1981, 22, 1961.
33. For some examples of asymmetric synthesis of cyclopropanes, see: (a) Nagasawa, T.; Handa, Y.; Onoguchi, S.; Ohba, S.; Suzuki, K. Synlett 1995, 739. (b) Charette, A.B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651. (c) Narjes, F.; Bolte, O.; Icheln, D.; König, W.A., Schaumann, E. J. Org. Chem. 1993, 58, 626. (d) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (e) Romo, D.; Meyers, A.I. J. Org. Chem. 1992, 57, 6265. (f) Lambs, L.; Singh, N.P., Biellmann, J.F. J. Org. Chem. 1992, 57, 66301, and references cited. (g) Hayashi T.; Yamamoto, A., Ito, Y. Tetrahedron Lett. 1988, 29, 669. (h) Monpert, A.; Martelli, J.; Grée, R., Carrié, R. Tetrahedron Lett. 1981, 22, 1961.
34. For some examples of asymmetric synthesis of cyclopropanes, see: (a) Nagasawa, T.; Handa, Y.; Onoguchi, S.; Ohba, S.; Suzuki, K. Synlett 1995, 739. (b) Charette, A.B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651. (c) Narjes, F.; Bolte, O.; Icheln, D.; König, W.A., Schaumann, E. J. Org. Chem. 1993, 58, 626. (d) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (e) Romo, D.; Meyers, A.I. J. Org. Chem. 1992, 57, 6265. (f) Lambs, L.; Singh, N.P., Biellmann, J.F. J. Org. Chem. 1992, 57, 66301, and references cited. (g) Hayashi T.; Yamamoto, A., Ito, Y. Tetrahedron Lett. 1988, 29, 669. (h) Monpert, A.; Martelli, J.; Grée, R., Carrié, R. Tetrahedron Lett. 1981, 22, 1961.