Asymmetric synthesis of optically active vinyltetrahydrofurans via palladium-catalysed cyclisation of bis(hydroxymethyl)allylic carbonates

Optically active 3-alkyl-3-hydroxymethy1-5-vinyltetrahydrofurans were synthesised from the corresponding methyl or isobutyl carbonates of omega,omega-bis(hydroxymethyl)-alpha,beta-unsaturated alcohols via palladium-catalysed cyclisation. The use of chiral ligands gave the corresponding tetrahydrofuran derivatives, which had er values that ranged from moderate to good. (C) 2013 Elsevier Ltd. All rights reserved.