102080

1-propynyltributylstannane

One step of the total synthesis of Stemoamide reported by Jacobi and Lee, requires the use of 1-propynyltributylstannane (Scheme 1) (1). The reaction is achieved with an excellent yield.

 

The reaction of bistriflate (Scheme 2) with 1-propynylstannane affords to bicyclic enediyne (2).

 

1-Propynylstannane reacts with various Lewis acids. As an example, 1-propynyl-trichlorostannane has been prepared by reaction of SnCl4 with 1-propynylstannane (3).

 

 

 

References:
(1) P. A. Jacobi, K. Lee J. Am. Chem. Soc., 1997, 119, 3409.
(2) J. H. Ryan, P. J. Stang J. Org. Chem. ,1996, 61, 6162.
(3) L. Lassalle, T. Janati, J.-C. Guillemin J. Chem. Soc., Chem. Commun. ,1995, 699.