Chemistry Letters, Vol.43, No.6, 766-768, 2014
Highly Diastereoselective Synthesis of Chiral Furans with a Quaternary Carbon Substituent at the 2-Position Using 8-Phenylmenthol as the Chiral Auxiliary
The reaction of cis-4-oxo-2-pentenal and 8-phenylmenthyl 2-oxocyclopentane-1-carboxylate in the presence of a fluorinated cosolvent afforded the corresponding furan product with a high diastereoselectivity of up to 96% de. Other cyclic beta-ketoesters reacted in a likewise diastereoselective manner.