Synthesis of Secondary and Tertiary Alkyl Boronic Esters by gem‐Carboborylation: Carbonyl Compounds as Bis(electrophile) Equivalents. (12th July 2018)

• Record Type: Journal Article
• Authors: Shi, Dunfa; Wang, Lu; Xia, Chungu; Liu, Chao
• Is Part Of: Angewandte Chemie. Volume 130:Number 32(2018)
• Page Start: 10475
• Page End: 10479
• Publication Date: 2018-07-12
• Subjects: Alkylboronsäureester -- Asymmetrische Katalyse -- Bor -- Carboborylierung -- Kupfer-Katalyse; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201804684
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: An unprecedent gem ‐carboborylation of aldehydes and ketones provides access to various secondary and tertiary alkyl boronic esters. The addition of B2 pin2 to a carbonyl compound generates α‐oxyl‐substituted alkyl boron species. Organolithium and Grignard reagents are then applied as C nucleophiles for the 1, 2‐metalate rearrangement process. The organolithium reagents can also be generated by C−H lithiation or halogen/lithium exchange. The use of chiral ligands led to the generation of chiral alkyl boronic esters in enantioenriched form, demonstrating that the enantioselectivity of this transformation is catalyst‐controlled.