The reaction of crotyltrialkylstannanes (1) with aldehydes in the presence of BF3, OEt2, produces the corresponding erythro homoallyl alcohols (2) predominantly regardless of the geometry of the double bond. Further, the Lewis acid mediated reaction exhibits the enhanced Cram selectivity in comparison with other allylic organometallic reactions which proceed in the absence of Lewis acids. Use of AlCl3-i-PrOH as the Lewis acid entirely ...
[Dobbs, Adrian P.; Guesne, Sebastien J. J.; Parker, Robert J.; Skidmore, John; Stephenson, Richard A.; Hursthouse, Mike B. Organic and Biomolecular Chemistry, 2010 , vol. 8, # 5 p. 1064 - 1080]
[Ewing, James C.; Ferguson, Gregory S.; Moore, Douglas W.; Schultz, Frederick W.; Thompson, David W. Journal of Organic Chemistry, 1985 , vol. 50, # 12 p. 2124 - 2128]
![but-2-enyl-[(tri-n-butyl)]-stannane Structure](https://image.chemsrc.com/caspic/311/35998-93-7.png)
