Reported herein is a photochemical cascade process that combines the excited-state and ground-state reactivity of chiral organocatalytic intermediates. This strategy directly converts racemic cyclopropanols and α,β-unsaturated aldehydes into stereochemically dense cyclopentanols with exquisite stereoselectivity. Mechanistic investigations have enabled elucidating the origin of the stereoconvergence, which is governed by a kinetic resolution process.
Keywords: cascade reactions; kinetic resolution; organocatalysis; photochemistry; radicals.
© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.