Enantiospecific ring expansion of oxetanes: Stereoselective synthesis of tetrahydrofurans

Heterocycles

Volumn 42, Issue 1, 1996, Pages 305-317

  Ito, Katsuji ^a   Yoshitake, Miwa ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001208193     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s35     Document Type: Article

References (18)

1. For the review, see: D. J. Faulkner, Nat. Prod. Rep., 1993, 10, 497 and references cited therein.
2. For the review, see: T. L. B. Boivin, Tetrahedron, 1987, 43, 3309 and references cited therein.
3. P. A. Bartlett, 'Asymmetric Synthesis,' Vol. 3, ed by J. D. Morrison, Academic Press, New York, 1984, pp. 342-449.
4. a) H. Nozaki, H. Takaya, and R. Noyori, Tetrahedron Lett., 1965, 2563;
5. b) H. Nozaki, S. Moriuti, H. Takaya, and R. Noyori, ibid., 1966, 5239;
6. c) H. Nozaki, H. Takaya, and R. Noyori, Tetrahedron, 1966, 22, 3393;
7. d) H. Nozaki, H. Takaya, S. Moriuti, and R. Noyori, ibid., 1968, 24, 3655.
8. For the review, see: A. Togni and L. M. Venanzi, Angew. Chem., Int. Ed. Engl., 1994, 33, 497 and references cited therein.
9. a) K. Ito, S. Tabuchi, and T. Katsuki, Synlett, 1992, 575;
10. b) K. Ito and T. Katsuki, Tetrahedron Lett., 1993, 34, 2661;
11. c) K. Ito and T. Katsuki, Synlett, 1993, 638.
12. Preliminary results have been communicated: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857.
13. A. I. Meyers and G. Garcia-Munoz, J. Org. Chem., 1964, 29, 1435.
14. M. Tiecco, L. Testaferri, M. Tingoli, D. Chianelli, and M. Montanucci, Synthesis, 1984, 736.
15. In the following Scheme, y and z stand for the diastereoface selectivity of the carbenoid species and Thus face selectivity (% de) of carbenoids is: With (S)-oxetane, % de= [y - (1-y)] × 100 = [2y - 1] × 100 = 72 With (R)-oxetane, % de= [z - (1-z)] × 100 = [2z - 1] × 100 = 84
16. H. Fritschi, U. Leutenegger, and A. Pfaltz, Helv. Chim. Acta, 1988, 71, 1553.
17. R. G. Salomon and J. K. Kochi, J. Am. Chem. Soc., 1973, 95, 3300.
18. P. Picard, D. Leclercq, J. -P. Bats, and J. Moulines, Synthesis, 1981, 550.