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.
L. Woźniak, G. Magagnano, P. Melchiorre
Angew. Chem. Int. Ed. 2018, 57, 1068-1072
DOI:
10.1002/anie.201711397
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