Masked allylic zinc reagents

Abstract

The preparation of allylic zinc reagents using the fragmentation of sterically hindered tertiary homoallylic alcohols is described

References

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2. Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207.
3. For reaction of Grignard reagents see: R. A. Benkeser and M. P. Siklosi, J. Org. Chem., 1976, 41, 3212; R. A. Benkeser, M. P. Siklosi and E. C. Mozdzen, J. Am. Chem. Soc., 1978, 100, 2134; R. A. Benkeser, W. G. Young, W. E. Broxterman, D. A. Jones and S. J. Piaseczynski, J. Am. Chem. Soc., 1969, 91, 132; F. Barbot and P. Miginiac, Bull. Chim. Soc. Fr., 1977, 113.
4. F. Gerard and P. Miginiac, Bull. Chim. Soc. Fr., 1974, 2527; F. Gerard and P. Miginiac, Bull. Chim. Soc. Fr., 1974, 1924.
5. (a) F. Barbot and P. Miginiac, Tetrahedron Lett., 1975, 3829; (b) P. Miginiac and C. Bouchoule, Bull. Chim. Soc. Fr., 1968, 4675; (c) F. Barbot and P. Miginiac, J. Organomet. Chem., 1977, 132, 445.
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7. J. Nokami, K. Yoshizane, H. Matsuura and S. Sumida, J. Am. Chem. Soc., 1998, 120, 6609.
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9. These reagents were prepared from 3-tert-butyl-2,2,5-trimethylhex-5-en-3-ol by NBS allylic bromination and displacement with the appropriate zinc-copper reagent (ref. 11).
10. A patent has been filed with Chemetall Gmbh (Frankfurt).
11. P. Knochel, M. C. P. Yeh, S. C. Berk and J. Talbert, J. Org. Chem., 1988, 53, 2390.