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Light‐Driven Enantioselective Synthesis of Pyrroline Derivatives by a Radical/Polar Cascade Reaction
Author(s) -
Rodríguez Ricardo I.,
Mollari Leonardo,
Alemán José
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202013020
Subject(s) - enantioselective synthesis , chemistry , electrophile , pyrroline , rhodium , stereoselectivity , combinatorial chemistry , catalysis , cascade , cascade reaction , atom economy , hydrogen atom , organic chemistry , alkyl , chromatography
Herein, a light‐driven, atom‐economical process that provides access to enantiomerically enriched substituted chiral 1‐pyrroline derivatives is introduced. The strategy involves the distal functionalization of acyl heterocycles through a hydrogen‐atom transfer (HAT) process and the use of tailor‐made ketimines as reliable electrophilic partners. This transformation is translated into an enantiomerically controlled radical/polar cascade reaction in which water is produced as the sole by‐product and stereoselectivity is dictated by coordination to a chiral‐at‐rhodium catalyst.