Synthesis of cyclopropanols via cyclopropanation of zinc enolates

Tetrahedron Letters

Volumn 39, Issue 29, 1998, Pages 5253-5256

  Ito, Saeko ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANOLOL; UNCLASSIFIED DRUG;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032537708     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01036-3     Document Type: Article

References (33)

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2. The Chemistry of the Cyclopropyl Group; Patai, S.; Rappoport, Z. Eds; Wiley; New York, 1987.
3. 2. Titanium-mediated synthesis of cyclopropanol. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244-2245; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294-298; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234; Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428-1430; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345-9346; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919-9920; Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291-292; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 117, 4198-4199; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079-6082; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849-1852.
4. 2. Titanium-mediated synthesis of cyclopropanol. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244-2245; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294-298; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234; Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428-1430; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345-9346; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919-9920; Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291-292; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 117, 4198-4199; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079-6082; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849-1852.
5. 2. Titanium-mediated synthesis of cyclopropanol. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244-2245; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294-298; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234; Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428-1430; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345-9346; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919-9920; Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291-292; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 117, 4198-4199; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079-6082; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849-1852.
6. 2. Titanium-mediated synthesis of cyclopropanol. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244-2245; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294-298; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234; Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428-1430; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345-9346; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919-9920; Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291-292; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 117, 4198-4199; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079-6082; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849-1852.
7. 2. Titanium-mediated synthesis of cyclopropanol. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244-2245; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294-298; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234; Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428-1430; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345-9346; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919-9920; Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291-292; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 117, 4198-4199; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079-6082; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849-1852.
8. 2. Titanium-mediated synthesis of cyclopropanol. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244-2245; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294-298; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234; Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428-1430; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345-9346; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919-9920; Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291-292; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 117, 4198-4199; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079-6082; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849-1852.
9. 2. Titanium-mediated synthesis of cyclopropanol. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244-2245; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294-298; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234; Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428-1430; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345-9346; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919-9920; Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291-292; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 117, 4198-4199; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079-6082; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849-1852.
10. 2. Titanium-mediated synthesis of cyclopropanol. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244-2245; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294-298; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234; Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428-1430; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345-9346; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919-9920; Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291-292; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 117, 4198-4199; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079-6082; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849-1852.
11. 2. Titanium-mediated synthesis of cyclopropanol. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244-2245; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294-298; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234; Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428-1430; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345-9346; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919-9920; Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291-292; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 117, 4198-4199; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079-6082; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849-1852.
12. 2. Titanium-mediated synthesis of cyclopropanol. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244-2245; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294-298; Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234; Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428-1430; Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345-9346; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919-9920; Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291-292; Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 117, 4198-4199; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079-6082; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849-1852.
13. 3. From cyclopropyl metallic compounds. Imai, T.; Mineta, H.; Nishida, S. J. Org. Chem. 1990, 55, 4986-4988; Fontani, P.; Carboni, B.; Vaultier, M.; Maas, G. Synthesis 1991, 605-609; Pietruszka, J.; Widenmeyer, M. Synlett 1997, 997-979; Hirabayashi, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1997, 38, 461-464;
14. 3. From cyclopropyl metallic compounds. Imai, T.; Mineta, H.; Nishida, S. J. Org. Chem. 1990, 55, 4986-4988; Fontani, P.; Carboni, B.; Vaultier, M.; Maas, G. Synthesis 1991, 605-609; Pietruszka, J.; Widenmeyer, M. Synlett 1997, 997-979; Hirabayashi, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1997, 38, 461-464;
15. 3. From cyclopropyl metallic compounds. Imai, T.; Mineta, H.; Nishida, S. J. Org. Chem. 1990, 55, 4986-4988; Fontani, P.; Carboni, B.; Vaultier, M.; Maas, G. Synthesis 1991, 605-609; Pietruszka, J.; Widenmeyer, M. Synlett 1997, 997-979; Hirabayashi, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1997, 38, 461-464;
16. 3. From cyclopropyl metallic compounds. Imai, T.; Mineta, H.; Nishida, S. J. Org. Chem. 1990, 55, 4986-4988; Fontani, P.; Carboni, B.; Vaultier, M.; Maas, G. Synthesis 1991, 605-609; Pietruszka, J.; Widenmeyer, M. Synlett 1997, 997-979; Hirabayashi, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1997, 38, 461-464;
17. 4. Cyclopropanation of silyl enolates into cyclopropyl silyl ethers. Murai, S.; Aya, T.; Sonoda, N. J. Org. Chem. 1973, 38, 4354-4356; LeGoaller, R.; Pierre, J. -L. Bull. Soc. Chim. Fr. 1973, 1531-1532; Rubottom, G. H.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; Girad, C.; Conia, J. M. Tetrahedron Lett. 1974, 3327-3328.
18. 4. Cyclopropanation of silyl enolates into cyclopropyl silyl ethers. Murai, S.; Aya, T.; Sonoda, N. J. Org. Chem. 1973, 38, 4354-4356; LeGoaller, R.; Pierre, J. -L. Bull. Soc. Chim. Fr. 1973, 1531-1532; Rubottom, G. H.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; Girad, C.; Conia, J. M. Tetrahedron Lett. 1974, 3327-3328.
19. 4. Cyclopropanation of silyl enolates into cyclopropyl silyl ethers. Murai, S.; Aya, T.; Sonoda, N. J. Org. Chem. 1973, 38, 4354-4356; LeGoaller, R.; Pierre, J. -L. Bull. Soc. Chim. Fr. 1973, 1531-1532; Rubottom, G. H.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; Girad, C.; Conia, J. M. Tetrahedron Lett. 1974, 3327-3328.
20. 4. Cyclopropanation of silyl enolates into cyclopropyl silyl ethers. Murai, S.; Aya, T.; Sonoda, N. J. Org. Chem. 1973, 38, 4354-4356; LeGoaller, R.; Pierre, J. -L. Bull. Soc. Chim. Fr. 1973, 1531-1532; Rubottom, G. H.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097-2099; Girad, C.; Conia, J. M. Tetrahedron Lett. 1974, 3327-3328.
21. 5. Imamoto, T.; Takeyama, T.; Koto, H. Tetrahedron Lett. 1986, 27, 3243-3246; Imamoto, T.; Takiyama, N. Tetrahedron Lett. 1987, 28, 1307-1308. Very recently, conversion of β-keto esters to γ-keto esters involving cyclopropanation of zinc enolate. Brogan, J. B.; Zercher, C. K. J. Org. Chem. 1997, 62, 6444-6446.
22. 5. Imamoto, T.; Takeyama, T.; Koto, H. Tetrahedron Lett. 1986, 27, 3243-3246; Imamoto, T.; Takiyama, N. Tetrahedron Lett. 1987, 28, 1307-1308. Very recently, conversion of β-keto esters to γ-keto esters involving cyclopropanation of zinc enolate. Brogan, J. B.; Zercher, C. K. J. Org. Chem. 1997, 62, 6444-6446.
23. 5. Imamoto, T.; Takeyama, T.; Koto, H. Tetrahedron Lett. 1986, 27, 3243-3246; Imamoto, T.; Takiyama, N. Tetrahedron Lett. 1987, 28, 1307-1308. Very recently, conversion of β-keto esters to γ-keto esters involving cyclopropanation of zinc enolate. Brogan, J. B.; Zercher, C. K. J. Org. Chem. 1997, 62, 6444-6446.
24. 6. Aoki, Y.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 463-464.
25. 7. Simmons, H. E.; Cairns, T. L.; Vladuchick, S. A.; Hoiness, C. M. Org. React. 1973, 20, 1-131; Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53-58.
26. 7. Simmons, H. E.; Cairns, T. L.; Vladuchick, S. A.; Hoiness, C. M. Org. React. 1973, 20, 1-131; Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53-58.
27. 1H NMR experiment. Thus, the reason for the stereoselective formation of cis-cyclopropanol 2a (c/t = 93/7) is not clear at this stage.
28. 9. Acid catalyzed opening of cyclopropanols, see. Whitlock, Jr., H. W.; Overman, L. E. J. Org. Chem. 1962, 34, 1962-1963; DePuy, C. H.; Breitbeil, F. W.; DeBruin, K. R. J. Am. Chem. Soc. 1966, 88, 3347-3354.
29. 9. Acid catalyzed opening of cyclopropanols, see. Whitlock, Jr., H. W.; Overman, L. E. J. Org. Chem. 1962, 34, 1962-1963; DePuy, C. H.; Breitbeil, F. W.; DeBruin, K. R. J. Am. Chem. Soc. 1966, 88, 3347-3354.
30. 10. 1,4-Addition of trialkylzincate, see. Isobe, M.; Kondo, S.; Nagasawa, N.; Goto, T. Chem. Lett. 1977, 679-682; Watson, R. A.; Kjonaas, R. A. Tetrahedron Lett. 1986, 27, 1437-1440; Kjonaas, R. A.; Vawter, E. J. J. Org. Chem. 1986, 51, 3993-3996; Tückmantcl, W.; Oshima, K.; Nozaki, H. Chem. Ber. 1986, 119, 1581-1593.
31. 10. 1,4-Addition of trialkylzincate, see. Isobe, M.; Kondo, S.; Nagasawa, N.; Goto, T. Chem. Lett. 1977, 679-682; Watson, R. A.; Kjonaas, R. A. Tetrahedron Lett. 1986, 27, 1437-1440; Kjonaas, R. A.; Vawter, E. J. J. Org. Chem. 1986, 51, 3993-3996; Tückmantcl, W.; Oshima, K.; Nozaki, H. Chem. Ber. 1986, 119, 1581-1593.
32. 10. 1,4-Addition of trialkylzincate, see. Isobe, M.; Kondo, S.; Nagasawa, N.; Goto, T. Chem. Lett. 1977, 679-682; Watson, R. A.; Kjonaas, R. A. Tetrahedron Lett. 1986, 27, 1437-1440; Kjonaas, R. A.; Vawter, E. J. J. Org. Chem. 1986, 51, 3993-3996; Tückmantcl, W.; Oshima, K.; Nozaki, H. Chem. Ber. 1986, 119, 1581-1593.
33. 10. 1,4-Addition of trialkylzincate, see. Isobe, M.; Kondo, S.; Nagasawa, N.; Goto, T. Chem. Lett. 1977, 679-682; Watson, R. A.; Kjonaas, R. A. Tetrahedron Lett. 1986, 27, 1437-1440; Kjonaas, R. A.; Vawter, E. J. J. Org. Chem. 1986, 51, 3993-3996; Tückmantcl, W.; Oshima, K.; Nozaki, H. Chem. Ber. 1986, 119, 1581-1593.