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Expedient Dual Co/Organophotoredox Catalyzed Stereoselective Synthesis of All‐Carbon Quaternary Centers
Author(s) -
Cristòfol Àlex,
Limburg Bart,
Kleij Arjan W.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202103479
Subject(s) - stereocenter , stereoselectivity , quaternary carbon , catalysis , chemistry , combinatorial chemistry , aldehyde , carbon fibers , reagent , organic chemistry , enantioselective synthesis , materials science , composite number , composite material
An efficient and attractive Co/organophotoredox dual catalysis protocol has been developed allowing the stereoselective access to a wide variety of syn‐configured 1,3‐diols featuring quaternary carbon centers. The synthesis of the target molecules is achieved under ambient reaction conditions using modular and accessible reagents, substituted vinyl cyclic carbonates and aldehydes, and in short reaction times. Mechanistic control experiments suggest that the stereoselectivity can be rationalized via a preferred Zimmerman–Traxler transition state comprising a Co(allyl) species and an activated aldehyde. This newly developed process thus expands the use of base metal catalysis in the construction of challenging quaternary carbon stereocenters.