Enantioselective palladaelectro-catalyzed C–H olefinations and allylations for N–C axial chirality. Issue 42 (13th October 2021)

• Record Type: Journal Article
• Authors: Dhawa, Uttam; Wdowik, Tomasz; Hou, Xiaoyan; Yuan, Binbin; Oliveira, João C. A.; Ackermann, Lutz
• Is Part Of: Chemical science. Volume 12:Issue 42(2021)
• Page Start: 14182
• Page End: 14188
• Publication Date: 2021-10-13
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc04687j
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Enantioselective palladaelectro-catalyzed C–H alkenylations and allylations were achieved by the means of an easily-accessible amino acid for the synthesis of N–C axially chiral indole biaryls. Abstract : Enantioselective palladaelectro-catalyzed C–H alkenylations and allylations were achieved with easily-accessible amino acids as transient directing groups. This strategy provided access to highly enantiomerically-enriched N–C axially chiral scaffolds under exceedingly mild conditions. The synthetic utility of our strategy was demonstrated by a variety of alkenes, while the versatility of our approach was reflected by atroposelective C–H allylations. Computational studies provided insights into a facile C–H activation by a seven-membered palladacycle.