Abstract
The reaction between allylstannanes and α,β-unsaturated acyliron complexes has been examined. When the reaction is conducted in the presence of Lewis acids, [3+2] cycloaddition products are obtained with extremely high degrees of stereoselectivity. The [3+2] cycloadducts contain acyliron and organotin functionalities. The acyliron group is easily converted to the corresponding ester by treatment with N-bromosuccinimide in the presence of alcohols. The tributyltin group can be converted to a hydroxy group by treatment with bromine followed by treatment with peracids and amine bases; this transformation occurs with complete retention of stereochemistry
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