Stereospecific cyclopropanation reactions of stannyl-substituted acetals with alkenes via γ-elimination of tin

Synlett

Volumn , Issue 10, 1998, Pages 1057-1058

  Sugawara, Masanobu ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001870436     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1896     Document Type: Article

References (20)

1. (a) Pereyre, M.; Quintard, J-B.; Rahm, A. Tin in Organic Synthesis; Butterworth & Co.: London, 1987; p 235 and references cited therein.
2. Selected examples (b) Peterson, D. J.; Robbins, M. D.; Hansen, J. R. J. Organometal. Chem. 1974, 73, 237.
3. (c) Fleming, I.; Urch, C. Tetrahedron Lett. 1983, 24, 4591.
4. (d) Sato, T.; Watanabe, M.; Watanabe, T.; Onoda, Y.; Murayama, E. J. Org. Chem. 1988, 53, 1894.
5. (e) Plamondon, L.; Wuest, J. D. J. Org. Chem. 1991, 56, 2066.
6. Sugawara, M.; Yoshida, J. J. Am. Chem. Soc. 1997, 119, 11986.
7. (a) Clark, H. C.; Willis, C. J. J. Am. Chem. Soc. 1960, 82, 1888.
8. (b) Seyferth, D.; Dertouzos, H.; Suzuki, R.; Mui, J. Y. P. J. Org. Chem. 1967, 32, 2980.
9. (c) Seyferth, D.; Armbrecht, F. M.; Prokai, B.; Cross, R. J. J. Organometal. Chem. 1966, 6, 573.
10. (d) Seyferth, D.; Armbrecht, F. M. J. Am. Chem. Soc. 1969, 97, 2616.
11. (e) Seyferth, D.; Lambert, R. L. J. Organometal. Chem. 1975, 91, 31.
12. Stannyl substituted acetal 2a was prepared according to the literature procedure: (a) Shiner, C. S.; Tsunoda, T.; Goodman, B. A.; Ingham, S.; Lee, S-h.; Vorndam, P. E. J. Am. Chem. Soc. 1989, 111, 1381.
13. The other method: (b) Quintard, J. P.; Elissondo, B.; Mpegna, D. M. J. Ornanomet. Chem. 1983, 251, 175.
14. Wong, H. N. C.; Hon, M.; Tse, C.; Yip, Y. Chem. Rev. 1989, 89, 165.
15. Acetals 2b, 3a, and 3b were prepared by TsOH catalyzed transacetalization of 2a in the excess amount of the corresponding alcohols.
16. Doyle, M. P. Acc. Chem. Res. 1986, 19, 348.
17. Recently, it was reported that the reactions of α-stannyl cyclic acetals with allyl stannanes and enol silyl ethers afforded the corresponding products. Cintrat, J. C.; Blart, E.; Parrain, J. L.; Quintard, J. P. Tetrahedron 1997, 53, 7615.
18. Sugimura, T.; Futagawa, T.; Tai. A. Tetrahedron Lett. 1988, 29, 5775
19. The stereochemistry of 4a was determined by NOE experiment. The stereochemistry of 4b and that of 4c were also determined by NOE experiments.
20. 18O 238.1358, found 238.1367.