Iodocarbocyclization reaction

Reviews on Heteroatom Chemistry

Volumn 15, Issue , 1997, Pages 243-262

  Kitagawa, Osamu ^a   Inoue, Tadashi ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Catalytic asymmetric reaction; Chiral ligand; Diastereoselective reaction; Iodine; Iodocarbocyclization reaction; Stereospecific reaction; Titanium alkoxide

Indexed keywords

EID: 0030527155     PISSN: 09156151     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. M. J. Bougaylt: C.R. Held. Seances Acad. Sci. 139 864-870 (1904).
2. P. A. Bartlett: "Asymmetric Synthesis" (Ed). J. D. Morrison (Academic Press, Orland, 1984) 3 Chap. 6, pp.411-453.
3. G. Gardillo and M. Orena: Tetrahedron 46 3321-3408 (1990).
4. S. Kobayashi: J. Syn. Org. Chem. Jpn. 41 745-754 (1983).
5. J. Barluenga, J. M. Gonzalez, P. J. Campos and G. Asensio: Angew. Chem. Int. Ed. Engl. 24 319-320 (1985).
6. J. Barluenga, J. M. Gonzalez, P. J. Campos and G. Asensio: Angew. Chem. Int. Ed. Engl. 27 1546-1547 (1988).
7. D. P. Curran and C.-T. Chang: J. Org. Chem. 54 3140-3157 (1989).
8. J. Cossy and A. Thellend: Tetrahedron Lett. 31 1427-1428 (1990).
9. O. Kitagawa, T. Inoue and T. Taguchi: Tetrahedron Lett. 33 2167-2170 (1992).
10. O. Kitagawa, T. Inoue, K. Hirano and T. Taguchi: J. Org. Chem. 58 3106-3112 (1993).
11. T. Inoue, O. Kitagawa, O. Ochiai and T. Taguchi: Tetrahedron: Asymmetry 6 691-692 (1995).
12. 2 and NaI at high temperatures to give iodoalkylcyclopropane or cyclopentane derivatives. However, under their reaction conditions, mixtures of cyclized products and α-iodomalonates are often obtained. A. L. Beckwith and M. J. Zozer: Tetrahedron Lett. 33 4975-4978 (1992).
13. O. Kitagawa, T. Inoue and T. Taguchi: Tetrahedron Lett. 35 1059-1062 (1994).
14. A. R. Chamberlin, M. Dezube, P. Dussalt and M. C. MacMills: J. Am. Chem. Soc. 105 5819-5825 (1983).
15. H. J. Cunther, E. Gruntrum and V. Jager: Liebigs Ann. Chem. 15-30 (1984).
16. M. Labelle and Y. Guindon: J. Am. Chem. Soc. 111 2204-2210 (1989).
17. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune and K. B. Sharpless: J. Am. Chem. Soc. 109 5765-5780 (1987).
18. J. N. Marx and G. Mineskanian: J. Org. Chem. 47 3306-3310 (1982).
19. G. Linz, J. Weetman, A. F. A. Hady and G. Helmchen: Tetrahedron Lett. 30 5599-5602 (1989).
20. I. Ikeda and K. Kanematsu: J. Chem. Soc., Chem. Commun. 453-455 (1995).
21. H. Umezawa, T. Takeuchi and K. Nitta: J. Antibiot. Ser. A. 6 101-105 (1953).
22. M. C. Pirrug, S. E. Dunlap and U. P. Trink: Helv. Chim. Acta 1301-1310 (1989).
23. C. Fliche, J. Braun and F. Goffic: Syn. Commun. 21 1429-1432 (1991).
24. C. H. Stammer: Tetrahedron 46 2231-2254 (1990).
25. H. Kodama and Y. Shimohigashi: J. Syn. Org. Chem. Jpn. 52 180-191 (1994).
26. G. Quinkert, U. Scwarz, H. Stark, W. D. Geber, H. Baier, F. Adam and G. Durner: Angew. Chem. Int. Ed. Engl. 19 1029-1030 (1980).
27. G. Quinkert and H. Stark: Angew. Chem. Int. Ed. Engl. 22 637-655 (1983).
28. T. Inoue, O. Kitagawa, S. Kurumizawa, O. Ochiai and T. Taguchi: Tetrahedron Lett. 36 1479-1482 (1995).
29. Catalytic asymmetric reaction using Lewis acidity and basicity of chiral rare-metal alkoxide has been reported by Sasai and Shibasaki. M. Shibasaki and H. Sasai: J. Syn. Org. Chem. Jpn. 51 972-983 (1993).
30. K. Narasaka, M. Inoue and N. Okada: Chem. Lett. 1109-1112 (1986).
31. K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima and J. Sugimori: J. Am. Chem. Soc. 111 5340-5345 (1989).
32. B. Schmidt and D. Seebach: Angew. Chem. Int. Ed. Engl. 30 99-100 (1991).
33. B. Schmidt and D. Seebach: Angew. Chem. Int. Ed. Engl. 30 1321-1322 (1991).
34. T. Inoue, O. Kitagawa, O. Ochiai and T. Taguchi: Tetrahedron Lett 36 9333-9336 (1995).
35. An example of enantio-group selective halolactonization of an achiral substrate using a stoichiometric amount of chiral titanium alkoxide: O. Kitagawa, T. Hanano, K. Tanabe, M. Shiro and T. Taguchi: J. Chem. Soc., Chem. Commun. 1005-1006 (1992).
36. Review of enantioselective reactions using the chiral titanium reagent: K. Narasaka and N. Iwasawa: Organic Synthesis: Theory and Applications, (Ed.) T. Hudlicky (JAI Press Inc; London, 1993) pp.93-112 and see also ref. 37.
37. K. Mikami and T. Nakai: Synlett. 255-265 (1992).
38. Transition state model for the origin of enantioselectivity in the catalytic asymmetric reaction using a 1:1 complex of chiral 1,4-diol and Ti(IV) as a chiral Lewis acid is proposed: E. J. Corey and Y. Matsumura: Tetrahedron Lett. 32 6289-6292 (1991) and see also refs. 39 and 40.
39. D. Seebach, R. Dahinden, R. E. Marti, A. K. Beck, D. A. Plattner and F. N. M. Kuhnle: J. Org. Chem. 60 1778-1799 (1995).
40. K. V. Goathelf, R.G. Hazell and K. A. Jorgensen: J. Am. Chem. Soc. 117 4435-4436 (1995).