Cyclopropanation of tin-substituted acetals with olefinic alcohols via in situ transacetalization

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1717-1720

  Sugawara, Masanobu ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Carbonium ions; Cyclopropanation; Cyclopropanes; Stereospecificity

Indexed keywords

ACETAL; ALKENE; CYCLOPROPANE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033605173     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00035-0     Document Type: Article

References (20)

1. [1] T.-L. Ho, Tactics of Organic Synthesis, Wiley, New York, 1994, pp190-212.
2. [2] a) L. F. Tietze, and U. Beifuss, Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163;
3. b) L. F. Tietze Chem. Rev. 1996, 96, 115-136.
4. [3] a) H. C. Clark, and C. S. Willis, J. Am. Chem. Soc. 1960, 82, 1888-1891;
5. b) D. Seyferth, F. M. Armbrecht, B. Prokai, and R. J. Cross, J. Organometal. Chem. 1966, 6, 573;
6. c) D. Seyferth, H. Dertouzos, R. Suzuki, and J. Y. P. Mui, J. Org. Chem. 1967, 32, 2980-2984;
7. d) D. Seyferth, and F. M. Armbrecht, J. Am. Chem. Soc. 1969, 91, 2616-2623;
8. e) D. Seyferth, and R. L. Lambert, J. Organometal. Chem. 1975, 91, 31-45;
9. f) J. P. Quintard, B. Elissondo, and D. M. Mpegna, J. Organomet. Chem. 1983, 251, 175-187.
10. [4] M. Sugawara, and J. Yoshida, J. Am. Chem. Soc. 1997, 119, 11986-11987.
11. [5] M. Sugawara, and J. Yoshida, Synlett 1998, 1057-1059.
12. [6] Cyclization reactions via in-situ transacetalization have been reported, a) N. A. Nikolic, E. Gonda, C. P. D. Longford, N. T. Lane, and D. W. Thompson, J. Org. Chem. 1989, 54, 2748-2751;
13. b) A. Mekhalfia, I. E. Marko, and H. Adams, Tetrahedron Lett. 1991, 32, 4783-4786;
14. c) F. Perron-Sierra, M. A. Promo, V. A. Martin, K. F. Albizati, J. Org. Chem. 1991, 56, 6188-6199;
15. d) I. E. Markó, A. Mekhalfia, D. J. Bayston, and H. Adamas, J. Org. Chem. 1992, 57, 2211-2213;
16. e) T. Oriyama, A. Ishiwata, T. Sano, T. Matsuda, M. Takahashi, and G. Koga, Tetrahedron Lett. 1995, 36 5581-5584;
17. f) M. Suginome, T. Iwanami, and Y. Ito, J. Org. Chem., 1998, 63, 6096-6097.
18. [7] Stannyl substituted acetal 1 was prepared according to the literature procedure. C. S. Shiner, T. Tsunoda, B. A. Goodman, S. Ingham, S-h. Lee, and P. E. Vorndam, J. Am. Chem. Soc. 1989, 111, 1381-1392. Another method: ref. 3f.
19. [8] M. Pereyre, J-B. Quintard, and A. Rahm, Tin in Organic Synthesis, Butterworth & Co., London, 1987, p 235.
20. [9] A. H. Hoveyda, D. A. Evans, and G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.