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Kinetic Resolution and Dynamic Kinetic Resolution of γ‐Aryl‐Substituted Butenolides via Copper‐Catalyzed 1,4‐Hydroboration
Author(s) -
Lee Soyeon,
Ryu Do Hyun,
Yun Jaesook
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001353
Subject(s) - chemistry , kinetic resolution , hydroboration , racemization , aryl , catalysis , selectivity , copper , organic chemistry , amine gas treating , combinatorial chemistry , medicinal chemistry , enantioselective synthesis , alkyl
Kinetic resolution (KR) and dynamic kinetic resolution (DKR) of γ‐aryl and heteroaryl‐substituted butenolides via CuH‐catalyzed 1,4‐hydroboration using pinacolborane is reported. With a copper‐Ph‐BPE catalyst, selectivity factors were extremely high ( s =>400) with regard to the kinetic resolution of β‐methyl‐γ‐phenyl butenolide; DKR was possible in the presence of an amine base (DBU), which facilitated racemization of the starting unsaturated lactones. The reaction provided easy access to highly enantioenriched γ‐butyrolactones (>99% ee) containing β,γ‐substituents.