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Photo‐Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
Author(s) -
Bonilla Pablo,
Rey Yannick P.,
Holden Catherine M.,
Melchiorre Paolo
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808183
Subject(s) - iminium , enantioselective synthesis , chemistry , cascade , organocatalysis , reactivity (psychology) , adduct , combinatorial chemistry , radical , radical ion , photoredox catalysis , radical cyclization , photochemistry , catalysis , organic chemistry , ion , photocatalysis , medicine , alternative medicine , chromatography , pathology
Radical cascade processes are invaluable for their ability to rapidly construct complex chiral molecules from simple substrates. However, implementing catalytic asymmetric variants is difficult. Reported herein is a visible‐light‐mediated organocatalytic strategy that exploits the excited‐state reactivity of chiral iminium ions to trigger radical cascade reactions with high enantioselectivity. By combining two sequential radical‐based bond‐forming events, the method converts unactivated olefins and α,β‐unsaturated aldehydes into chiral adducts in a single step. The implementation of an asymmetric three‐component radical cascade further demonstrates the complexity‐generating power of this photochemical strategy.