4.7 Article

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

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 9, Pages 2377-2381

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202001353

Keywords

Copper; Dynamic kinetic resolution; Hydroboration; Kinetic resolution; Lactones

Funding

  1. National Research Foundation of Korea (NRF) [2019R1A2C2005706, 2019R1A4A2001440]
  2. National Research Foundation of Korea [2019R1A2C2005706] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

Ask authors/readers for more resources

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.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available