Stereospecific and stereoselective preparation of 2-(1-hydroxyalkyl)-1- alkylcyclopropanols from α,β-epoxy ketones and bis(iodozincio)methane

Angewandte Chemie - International Edition

Volumn 44, Issue 36, 2005, Pages 5860-5863

  Nomura, Kenichi ^a   Oshima, Koichiro ^a   Matsubara, Seijiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Diastereoselectivity; Epoxy ketones; Small ring systems; Zinc

Indexed keywords

KETONES; METHANE; ZINC;

DIASTEREOSELECTIVITY; EPOXY KETONES; SMALL RING SYSTEMS;

ORGANIC COMPOUNDS;

KETONE; METHANE; PROPANOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

KETONES; METHANE; MODELS, MOLECULAR; PROPANOLS; STEREOISOMERISM;

EID: 24944444307     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501644     Document Type: Article

References (30)

1. a) H. E. Simmons, R. D. Smith, J. Am. Chem. Soc. 1958, 80, 5323;
2. b) H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977;
3. c) A. B. Charette, A. Beauchemin, Org. React. 2001, 58, 1.
4. a) S. Matsubara, K. Oshima, K. Utimoto, J. Organomet. Chem. 2001, 617, 39;
5. S. Matsubara, J. Org. Synth. Soc. Jpn. 2000, 58, 118;
6. b) P. Knochel, J.-F. Normant, Tetrahedron Lett. 1986, 27, 4427
7. and P. Knochel, J.-F. Normant, Tetrahedron Lett. 1986, 27, 4431;
8. c) I. Marek, J.-F. Normant, Chem. Rev. 1996, 96, 3241;
9. d) I. Marek, J.-F. Normant in Organozinc Reagents. A Practical Approach (Eds.: P. Knochel, P. Jones), Oxford Uninersity Press, Oxford, 1999, p. 119.
10. a) D. Beruben, I. Marek, J.-F. Normant, N. Platzer, J. Org. Chem. 1995, 60, 2488;
11. b) D. Beruben, I. Marek, J.-F. Normant, N. Platzer, Tetrahedron Lett. 1993, 34, 7575.
12. a) K. Ukai, K. Oshima, S. Matsubara, J. Am. Chem. Soc. 2000, 122, 12047;
13. b) K. Nomura, K. Oshima, S. Matsubara, Tetrahedron Lett. 2004, 45, 5957;
14. c) S. Matsubara, K. Ukai, H. Fushimi, Y. Yokota, H. Yoshino, K. Oshima, K. Omoto, A. Ogawa, Y. Hioki, H. Fujimoto, Tetrahedron 2002, 58, 8255.
15. S. Matsubara, H. Yamamoto, K. Oshima, Angew. Chem. 2002, 114, 2961;
16. Angew. Chem. Int. Ed. 2002, 41, 2837.
17. T. Sato, T. Kikuchi, H. Tsujita, A. Kaetsu, N. Sootome, K. Nishida, K. Tachibana, E. Murayama, Tetrahedron 1991, 47, 3281.
18. max = 54.1°, R = 0.0371 for 4852 reflections (I > 2σ(I)).
19. 3N.
20. K. Ukai, D. Arioka, H. Yoshino, H. Fushimi, K. Oshima, K. Utimoto, S. Matsubara, Synlett 2001, 513.
21. a) K. Li, L. G. Hamann, M. Koreeda, Tetrahedron Lett. 1992, 33, 6569;
22. b) T. Nakata, T. Tanaka, T. Oishi, Tetrahedron Lett. 1981, 22, 7723;
23. c) D. E. Chavez, E. N. Jacobsen, Angew. Chem. 2001, 113, 3779;
24. Angew. Chem. Int. Ed. 2001, 40, 3667.
25. H. Fujii, K. Oshima, K. Utimoto, Chem. Lett. 1992, 967.
26. max = 54.1°, R = 0.0320 for 5098 reflections (I > 2σ(I)).
27. a) R. Tokunoh, H. Tomiyama, M. Sodeoka, M. Shibasaki, Tetrahedron Lett. 1996, 37, 2449;
28. b) A. Corsaro, U. Chiacchio, R. Adamo, Pistarà, A. Rescifina, R. Romeo, G. Catelani, F. D'Andrea, M. Mariani, E. Attolino, Tetrahedron 2004, 60, 3787.
29. S. Matsubara, Y. Yamamoto, K. Utimoto, Synlett 1998, 1471.
30. S. Matsubara, K. Oshima, H. Matsuoka, K. Matsumoto, K. Ishikawa, E. Matsubara, Chem. Lett. 2005, 34, 952.