Diastereo- and Enantioselective Synthesis of 1,2,3-Substituted Cyclopropanes with Zinc Carbenoids

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 10, 1997, Pages 1090-1092

  Charette, André B ^a   Lemay, Jacinthe ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Asymmetric synthesis; Carbenoids; Cyclopropanations; Iodine; Zinc

Indexed keywords

EID: 0030767994     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199710901     Document Type: Article

References (40)

1. The pyrethroids are among the most important class of natural products containing 1,2,3-substituted cyclopropane units: K. Naumann in Chemistry of Plant Protection, Vol. 5, Synthetic Pyrethroid Insecticides. (Eds.: G. Haug, H. Hoffmann), Springer, Heidelberg, 1990, p. 63.
2. For other examples of natural products containing 1,2,3-substituted cyclopropanes, see a) R. Kazlauskas, P. T. Murphy, R. J. Wells, J. F. Blount, Tetrahedron Lett. 1978, 19, 4155-4158; b) W. W. Epstein, L. A. Gaudioso, G. B. Brewster, J. Org. Chem. 1984, 49, 2748-2754; c) D. T. Connor, R. C. Greenough, M. von Strandtmann, ibid. 1977, 42, 3664-3669; d) H.-U. Reissig, Angew. Chem. 1996, 108, 1049-1051, and references therein; Angew. Chem. Int. Ed. Engl. 1996, 35, 971-973, and references therein.
3. For other examples of natural products containing 1,2,3-substituted cyclopropanes, see a) R. Kazlauskas, P. T. Murphy, R. J. Wells, J. F. Blount, Tetrahedron Lett. 1978, 19, 4155-4158; b) W. W. Epstein, L. A. Gaudioso, G. B. Brewster, J. Org. Chem. 1984, 49, 2748-2754; c) D. T. Connor, R. C. Greenough, M. von Strandtmann, ibid. 1977, 42, 3664-3669; d) H.-U. Reissig, Angew. Chem. 1996, 108, 1049-1051, and references therein; Angew. Chem. Int. Ed. Engl. 1996, 35, 971-973, and references therein.
4. For other examples of natural products containing 1,2,3-substituted cyclopropanes, see a) R. Kazlauskas, P. T. Murphy, R. J. Wells, J. F. Blount, Tetrahedron Lett. 1978, 19, 4155-4158; b) W. W. Epstein, L. A. Gaudioso, G. B. Brewster, J. Org. Chem. 1984, 49, 2748-2754; c) D. T. Connor, R. C. Greenough, M. von Strandtmann, ibid. 1977, 42, 3664-3669; d) H.-U. Reissig, Angew. Chem. 1996, 108, 1049-1051, and references therein; Angew. Chem. Int. Ed. Engl. 1996, 35, 971-973, and references therein.
5. For other examples of natural products containing 1,2,3-substituted cyclopropanes, see a) R. Kazlauskas, P. T. Murphy, R. J. Wells, J. F. Blount, Tetrahedron Lett. 1978, 19, 4155-4158; b) W. W. Epstein, L. A. Gaudioso, G. B. Brewster, J. Org. Chem. 1984, 49, 2748-2754; c) D. T. Connor, R. C. Greenough, M. von Strandtmann, ibid. 1977, 42, 3664-3669; d) H.-U. Reissig, Angew. Chem. 1996, 108, 1049-1051, and references therein; Angew. Chem. Int. Ed. Engl. 1996, 35, 971-973, and references therein.
6. For other examples of natural products containing 1,2,3-substituted cyclopropanes, see a) R. Kazlauskas, P. T. Murphy, R. J. Wells, J. F. Blount, Tetrahedron Lett. 1978, 19, 4155-4158; b) W. W. Epstein, L. A. Gaudioso, G. B. Brewster, J. Org. Chem. 1984, 49, 2748-2754; c) D. T. Connor, R. C. Greenough, M. von Strandtmann, ibid. 1977, 42, 3664-3669; d) H.-U. Reissig, Angew. Chem. 1996, 108, 1049-1051, and references therein; Angew. Chem. Int. Ed. Engl. 1996, 35, 971-973, and references therein.
7. a) S. Hanessian, D. Andreotti, A. Gomtsyan, J. Am. Chem. Soc. 1995, 117, 10393-10394;
8. b) A. Krief, P. Lecomte, Tetrahedron Lett. 1993, 34, 2695-2698;
9. c) D. Romo, A. I. Meyers, J. Org. Chem. 1992, 57, 6265-6270.
10. a) M. A. Doyle, R. E. Austin, A. S. Bailey, M. P. Dwyer, A. B. Dyatkin, A. V. Kalinin, M. M. Y. Kwan, S. Liras, C. J. Oalmann, R. J. Pieters, M. N. Protopopova, C. E. Raab, G. H. P. Roos, Q.-L. Zhou, S. F. Martin, J. Am. Chem. Soc. 1995, 117, 5763-5775;
11. b) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345.
12. For other approaches, see a) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org. Chem. 1995, 60, 2488-2501; b) A. Krief, W. Dumont, L. Provins, Synlett 1995, 121-122; c) M. Kawana, H. Kuzuhara, Synthesis 1995, 543-552; d) H. Gooding, S. M. Roberts, R. Storer, J. Chem. Soc. Perkin Trans. 1 1994, 1891-1892; e) L. Lambs, N. P. Singh, J.-F. Biellmann, J. Org. Chem. 1992, 57, 6301-6304.
13. For other approaches, see a) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org. Chem. 1995, 60, 2488-2501; b) A. Krief, W. Dumont, L. Provins, Synlett 1995, 121-122; c) M. Kawana, H. Kuzuhara, Synthesis 1995, 543-552; d) H. Gooding, S. M. Roberts, R. Storer, J. Chem. Soc. Perkin Trans. 1 1994, 1891-1892; e) L. Lambs, N. P. Singh, J.-F. Biellmann, J. Org. Chem. 1992, 57, 6301-6304.
14. For other approaches, see a) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org. Chem. 1995, 60, 2488-2501; b) A. Krief, W. Dumont, L. Provins, Synlett 1995, 121-122; c) M. Kawana, H. Kuzuhara, Synthesis 1995, 543-552; d) H. Gooding, S. M. Roberts, R. Storer, J. Chem. Soc. Perkin Trans. 1 1994, 1891-1892; e) L. Lambs, N. P. Singh, J.-F. Biellmann, J. Org. Chem. 1992, 57, 6301-6304.
15. For other approaches, see a) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org. Chem. 1995, 60, 2488-2501; b) A. Krief, W. Dumont, L. Provins, Synlett 1995, 121-122; c) M. Kawana, H. Kuzuhara, Synthesis 1995, 543-552; d) H. Gooding, S. M. Roberts, R. Storer, J. Chem. Soc. Perkin Trans. 1 1994, 1891-1892; e) L. Lambs, N. P. Singh, J.-F. Biellmann, J. Org. Chem. 1992, 57, 6301-6304.
16. For other approaches, see a) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org. Chem. 1995, 60, 2488-2501; b) A. Krief, W. Dumont, L. Provins, Synlett 1995, 121-122; c) M. Kawana, H. Kuzuhara, Synthesis 1995, 543-552; d) H. Gooding, S. M. Roberts, R. Storer, J. Chem. Soc. Perkin Trans. 1 1994, 1891-1892; e) L. Lambs, N. P. Singh, J.-F. Biellmann, J. Org. Chem. 1992, 57, 6301-6304.
17. H. E. Simmons, T. L. Cairns, S. A. Vladuchick, C. M. Hoiness, Org. React. 1973, 20, 1-131.
18. 2Zn, see S. E. Denmark, B. L. Christenson, S. P. O'Connor, M. Noriaki, Pure Appl. Chem. 1996, 68, 23-27. In this example, a 65:35 diastereomeric mixture was obtained in 58% yield (major diastereomer: 12% ee: minor: 61% ee).
19. T. Sugimura, T. Katagiri, A. Tai, Tetrahedron Lett. 1992, 33, 267-268.
20. For a review on the role of zinc carbenoids in organic synthesis, see W. B. Motherwell, C. J. Nutley, Contemp. Org. Synth. 1994, 1, 219-241.
21. a) J. Nishimura, N. Kawabata, J. Furukawa, Tetrahedron 1969, 25, 2647-2659;
22. b) J. Furukawa, N. Kawabata, T. Fujita, ibid. 1970, 26, 243-250;
23. c) J. Furukawa, N. Kawabata, J. Nishimura, Tetrahedron Lett. 1968, 3495-3498.
24. For related examples, see a) U. Groth, U. U. Schöllkopf, T. Tiller, Liebigs Ann. Chem. 1991, 857-860; b) G. M. Rubottom, E. C. Beedle, C.-W. Kim, R. C. Mott, J. Am. Chem. Soc. 1985, 107, 4230-4233; c) E. C. Friederich, G. Biresaw, J. Org. Chem. 1982, 47, 1615-1618; d) N. Kawabata, T. Nakagawa, T. Nakao, S. Yamashita, ibid. 1977, 42, 3031-3035.
25. For related examples, see a) U. Groth, U. U. Schöllkopf, T. Tiller, Liebigs Ann. Chem. 1991, 857-860; b) G. M. Rubottom, E. C. Beedle, C.-W. Kim, R. C. Mott, J. Am. Chem. Soc. 1985, 107, 4230-4233; c) E. C. Friederich, G. Biresaw, J. Org. Chem. 1982, 47, 1615-1618; d) N. Kawabata, T. Nakagawa, T. Nakao, S. Yamashita, ibid. 1977, 42, 3031-3035.
26. For related examples, see a) U. Groth, U. U. Schöllkopf, T. Tiller, Liebigs Ann. Chem. 1991, 857-860; b) G. M. Rubottom, E. C. Beedle, C.-W. Kim, R. C. Mott, J. Am. Chem. Soc. 1985, 107, 4230-4233; c) E. C. Friederich, G. Biresaw, J. Org. Chem. 1982, 47, 1615-1618; d) N. Kawabata, T. Nakagawa, T. Nakao, S. Yamashita, ibid. 1977, 42, 3031-3035.
27. For related examples, see a) U. Groth, U. U. Schöllkopf, T. Tiller, Liebigs Ann. Chem. 1991, 857-860; b) G. M. Rubottom, E. C. Beedle, C.-W. Kim, R. C. Mott, J. Am. Chem. Soc. 1985, 107, 4230-4233; c) E. C. Friederich, G. Biresaw, J. Org. Chem. 1982, 47, 1615-1618; d) N. Kawabata, T. Nakagawa, T. Nakao, S. Yamashita, ibid. 1977, 42, 3031-3035.
28. A. B. Charette, H. Lebel, J. Org. Chem. 1995, 60, 2966-2967.
29. S. E. Denmark, J. P. Edwards, J. Org. Chem. 1991, 56, 6974-6981.
30. a) A. B. Charette, H. Juteau, J. Am. Chem. Soc. 1994, 116, 2651-2652;
31. b) A. B. Charette, S. Prescott, C. Brochu, J. Org. Chem. 1995, 60, 1081-1083.
32. The relative configuration of the major isomer was determined by NOE experiments and comparison with known compounds. The absolute configuration is postulated to be that shown, based on extrapolation of our earlier work [14].
33. a) P. Knochel, Chemtracts-Organic Chemistry 1995, 205-221;
34. b) P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188.
35. Halomethylzinc reagents have also been prepared and used as cyclopropanating reagents: a) T. Akiba, O. Tamura, M. Hashimoto, Y. Kobayashi, T. Katoh, K. Nakatani, M. Kamada, I. Hayakawa, S. Terashima, Tetrahedron 1994, 50, 3905-3914; b) S. Miyano, H. Hashimoto, Bull. Chem. Soc. Jpn. 1974, 47, 1500-1503; c) J. Nishimura, J. Furukawa, J. Chem. Soc. Chem. Commun. 1971, 1375-1376.
36. Halomethylzinc reagents have also been prepared and used as cyclopropanating reagents: a) T. Akiba, O. Tamura, M. Hashimoto, Y. Kobayashi, T. Katoh, K. Nakatani, M. Kamada, I. Hayakawa, S. Terashima, Tetrahedron 1994, 50, 3905-3914; b) S. Miyano, H. Hashimoto, Bull. Chem. Soc. Jpn. 1974, 47, 1500-1503; c) J. Nishimura, J. Furukawa, J. Chem. Soc. Chem. Commun. 1971, 1375-1376.
37. Halomethylzinc reagents have also been prepared and used as cyclopropanating reagents: a) T. Akiba, O. Tamura, M. Hashimoto, Y. Kobayashi, T. Katoh, K. Nakatani, M. Kamada, I. Hayakawa, S. Terashima, Tetrahedron 1994, 50, 3905-3914; b) S. Miyano, H. Hashimoto, Bull. Chem. Soc. Jpn. 1974, 47, 1500-1503; c) J. Nishimura, J. Furukawa, J. Chem. Soc. Chem. Commun. 1971, 1375-1376.
38. P. Charreau, M. Julia, J. N. Verpeaux, Bul.l Soc. Chim. Fr. 1990, 127, 275-282.
39. 3N (94%).
40. Quite surprisingly, the desired cyclopropane was obtained only in the presence of the chiral ligand. It is conceivable that the chiral ligand plays the important role of stabilizing the reagent. 1-Triisopropylsilyloxy-2-propene that is presumably generated by the decomposition of the carbene was isolated as the major by-product.