Reductivealdolreactions on aromatic heterocycles
Donohoe, Timothy J.
Ace, Karl W.
Guyo, Paul M.
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The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductivealdolreaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn-aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography.