Synthesis of Chiral 2,3-Dihydrofurans via One-Pot Pd-Catalyzed Asymmetric Allylic Cycloaddition and a Retro-Dieckmann
Babar Hussain Shah1, Sardaraz Khan1, Can Zhao1
1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, and School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China.
Abstract:
An efficient method for the enantioselective synthesis of 2,3-dihydrofurans bearing a quaternary stereocenter has been developed via Pd-catalyzed asymmetric allylic cycloaddition and a retro-Dieckmann Fragmentation cascade. The asymmetric allylic cycloaddition of vinylethylene carbonates with 3-cyanochromone followed by base-assisted retro-Dieckmann fragmentation proceeded smoothly via a one-pot process to produce chiral 3,4-disubstituted 2,3-dihydrofurans in high yields with excellent enantioselectivities.
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