1533422-35-3Relevant academic research and scientific papers
Enantioselective γ-C(sp3)-H activation of alkyl amines via Pd(II)/Pd(0) catalysis
Shao, Qian,Wu, Qing-Feng,He, Jian,Yu, Jin-Quan
, p. 5322 - 5325 (2018/05/03)
Pd(II)-catalyzed enantioselective γ-C(sp3)-H cross-coupling of alkyl amines via desymmetrization and kinetic resolution has been realized for the first time using chiral acetyl-protected aminomethyl oxazoline ligands (APAO). A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners. The chiral γ-arylated alkylamine products are further transformed into chiral 2-substituted 1,2,3,4-tetra-hydroquinolines and spiro-pyrrolidines as important structural motifs in natural products and biologically active molecules.
Ligand-enabled cross-coupling of C(sp 3)-H bonds with arylboron reagents via Pd(II)/Pd(0) catalysis
Chan, Kelvin S. L.,Wasa, Masayuki,Chu, Ling,Laforteza, Brian N.,Miura, Masanori,Yu, Jin-Quan
, p. 146 - 150 (2014/02/14)
There have been numerous developments in C-H activation reactions in the past decade. Attracted by the ability to functionalize molecules directly at ostensibly unreactive C-H bonds, chemists have discovered reaction conditions that enable reactions of C(sp 2)-H and C(sp 3)-H bonds with a variety of coupling partners. Despite these advances, the development of suitable ligands that enable catalytic C(sp 3)-H bond functionalization remains a significant challenge. Herein we report the discovery of a mono-N-protected amino acid ligand that enables Pd(II)-catalysed coupling of γ-C(sp 3)-H bonds in triflyl-protected amines with arylboron reagents. Remarkably, no background reaction was observed in the absence of ligand. A variety of amine substrates and arylboron reagents were cross-coupled using this method. Arylation of optically active substrates derived from amino acids also provides a potential route for preparing non-proteinogenic amino acids.
