Kinetic Resolution and Dynamic Kinetic Resolution of γ‐Aryl‐Substituted Butenolides via Copper‐Catalyzed 1,4‐Hydroboration | Zendy

Lee Soyeon | Zendy; Ryu Do Hyun | Zendy; Yun Jaesook | Zendy

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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.

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