101020

3-methyl-2-butenyltributylstannane 

3-Methyl-2-butenyltributylstannane is a remarkable agent for generating prenylating species, via an allylic transposition of a reverse prenylboron reagent, generated in situ (Scheme 1) (1).

 

With Lewis acids, the formation of a- or g-products is dependent on the strength of the acid (Scheme 2) (2).

 

References

(1)	K. M. Depew, S. J. Danishefsky, N. Rosen, L. Sepp-Lorenzino J. Am. Chem. Soc., 1996, 118, 12463.
(2)	S. Le Serre , J.-C. Guillemin, T. Karpati, L. Soos, L. Nyulaszi, T. Veszpremi J. Org. Chem. 1998, 63, 59-68.