Search

A Pd-catalyzed atroposelective C-H allylation with 1,1-disubstituted alkenes was developed for the synthesis of enantioenriched N -aryl peptoid atropisomers via β-H elimination using commercially available and inexpensive L- p Glu-OH as a chiral ligand. Exclusive allylic selectivity was achieved. Additionally, a series of enantioenriched N -aryl peptoid atropisomers were obtained in synthetically useful yields with excellent enantioselectivities (up to 90% yield and 97% ee).

A scalable and unified strategy is described for the synthesis of (-)-quinocarcin, an important tetrahydroisoquinoline antitumor alkaloid. The strategy allows the practical formal synthesis of (-)-quinocarcin in 13 steps and 4.8% overall yield using N-phthaloyl-l-alanine as a chiral pool. It features the gram-scale and stereoselective synthesis of the tetrahydroisoquinoline moiety (AB ring) via Pd-catalyzed C(sp 3 )-H arylation and Pictet-Spengler condensation and a Cu(I)-catalyzed exo-selective [C + NC + CC] coupling reaction to generate the chiral pyrrolidine motif (D ring).