The generation and trapping of organozinc carbenoids from orthoformates: a novel alkoxycyclopropanation reaction

Abstract

Alkoxycyclopropanes are readily prepared by reaction of an orthoformate with an alkene in the presence of Me₃SiCl and zinc.

References

1. For a review, see C. J. Nutley and W. B. Motherwell, Contemp. Org. Synth., 1994, 219.
2. W. B. Motherwell, J. Chem. Soc., Chem. Commun., 1973, 935.
3. A. K. Banerjee, M. C. S. Carrasco, C. S. V. Frydrych-Houge and W. B. Motherwell, J. Chem. Soc., Chem. Commun., 1986, 803; C. A. M. Afonso, W. B. Motherwell, D. M. O'Shea and L. R. Roberts, Tetrahedron Lett., 1992, 33, 3899.
4. W. B. Motherwell and L. R. Roberts, J. Chem. Soc., Chem. Commun., 1992, 1582; W. B. Motherwell and L. R. Roberts, Tetrahedron Lett., 1995, 36, 1121.
5. R. Imwinkelried and L. S. Hegedus, Organometallics, 1988, 7, 702.
6. R. D. Theys and M. M. Hossain, Tetrahedron Lett., 1992, 33, 3447; H. Dy. F. Yang and M. M. Hossain, Synth. Commun., 1996, 26, 1371.
7. W. B. Motherwell, D. J. R. O'Mahony and M. E. Popkin, Tetrahedron Lett., 1998, 39, 5285.
8. E. Wenkert, Acc. Chem. Res., 1980, 30, 27.
9. S. W. Smith and M. S. Newman, J. Am. Chem. Soc., 1968, 90, 1249; M. Hahn and C. S. Hudson, J. Am. Chem. Soc., 1944, 66, 1909; S. A. Barker and E. D. Bourne, Adv. Carbohydr. Chem., 1952, 7, 137; M. S. Newman and R. S. Harper Jr., J. Am. Chem. Soc., 1958, 80, 6350.
10. H. E. Simmons, T. L. Cairns, S. A. Vladuchick and C. H. Hoiness, Org. React., 1973, 20, 1.
11. U. Schöllkopf and G. J. Lehmann, Tetrahedron Lett., 1962, 4, 165; U. Schöllkopf, J. Paust, A. Ali-Azrak and H. Schumacher, Chem. Ber., 1966, 99, 3391.
12. M. Brookhart and W. B. Studabaker, Chem. Rev., 1987, 87, 411.