Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 9, Pages 2377-2381Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202001353
Keywords
Copper; Dynamic kinetic resolution; Hydroboration; Kinetic resolution; Lactones
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Funding
- National Research Foundation of Korea (NRF) [2019R1A2C2005706, 2019R1A4A2001440]
- National Research Foundation of Korea [2019R1A2C2005706] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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This study reports the kinetic resolution (KR) and dynamic kinetic resolution (DKR) of gamma-aryl and heteroaryl-substituted butenolides via CuH-catalyzed 1,4-hydroboration. The use of a copper-Ph-BPE catalyst resulted in high selectivity factors for the kinetic resolution of beta-methyl-gamma-phenyl butenolide, and DKR was possible with an amine base (DBU) to obtain highly enantioenriched gamma-butyrolactones (>99% ee) containing beta,gamma-substituents.
Kinetic resolution (KR) and dynamic kinetic resolution (DKR) of gamma-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 beta-methyl-gamma-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 gamma-butyrolactones (>99% ee) containing beta,gamma-substituents.
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