Enantioselective Intramolecular Copper‐Catalyzed Borylacylation. Issue 42 (21st September 2018)

• Record Type: Journal Article
• Authors: Whyte, Andrew; Burton, Katherine I.; Zhang, Jingli; Lautens, Mark
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 42(2018)
• Page Start: 13927
• Page End: 13930
• Publication Date: 2018-09-21
• Subjects: asymmetric catalysis -- boron -- copper -- cyclizations -- heterocycles; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201808460
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: An enantioselective copper‐catalyzed intramolecular borylacylation is reported. The reaction proceeds through an initial enantioselective borylcupration of the styrene, followed by a nucleophilic attack on the tethered carbamoyl chloride. The products, chiral borylated 3, 3‐disubstituted oxindoles, were generated in excellent yields and enantioselectivities. The versatile carbon–boron bond provides a platform for a wide array of diversification. Abstract : Cu again : Chiral 3, 3‐disubstituted borylated oxindoles have been synthesized in good yields and enantioselectivities. The reaction employs a chiral copper catalyst for an enantioselective borylcupration followed by intramolecular acylation with a tethered carbamoyl chloride. The chiral oxindole products are readily diversifiable into a range of substituted oxindole products. pin=pinacol.