Preparation and reactions of water stable hypervalent 10-Sn-5 allyl ate complexes

Hypervalent 10-Sn-5 allyl and crotyl tin ate complexes bearing Martin ligands were prepared and found to be surprisingly stable in water. These compounds were found to react with aldehydes in the presence of weak Lewis acids such as LiBr to give the corresponding homoallyl alcohols. Product analysis of the reaction of the crotyl compounds indicated that the reaction occurred via a cyclic transition state unlike an acyclic transition state operative for widely utilized allyltrialkyltin reagents that are of ordinary valency. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:425–430, 2001