Unexpected temperature-dependent stereoselectivity in the thermolysis of 2-trialkylstannyl alcohols

Abstract

Thermolysis of substituted 2-trialkylstannyl alcohols reveals a complete reversal of selectivity between 100 and 160 °C i.e. an erythro 2-trialkylstannyl alcohol leads to an (E)-alkene at 100 °C or a (Z)-alkene at 160 °C; this unexpected result depends on the formation of trialkyltin alkoxide intermediates and allows the preparation of isomeric alkenes from the same precursor by simply changing the reaction temperature.