title: Expanding insight into asymmetric palladium-catalyzed allylic alkylation of N-heterocyclic molecules and cyclic ketones.
abstract: Eeny, meeny, miny ... enaminones! Lactams and imides have been shown to consistently provide enantioselectivities substantially higher than other substrate classes previously investigated in the palladium-catalyzed asymmetric decarboxylative allylic alkylation. Several new substrates have been designed to probe the contributions of electronic, steric, and stereoelectronic factors that distinguish the lactam/imide series as superior alkylation substrates (see scheme). These studies culminated in marked improvements on carbocyclic allylic alkylation substrates.
authors: Division of Chemistry and Chemical Engineering, California Institute of Technology, Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, 1200 E. California Blvd, MC 101-20, Pasadena, CA 91125, USA.
authors: Nathan B
authors: NB
authors: Bennett
authors: Douglas C
authors: DC
authors: Duquette
authors: Jimin
authors: J
authors: Kim
authors: Wen-Bo
authors: WB
authors: Liu
authors: Alexander N
authors: AN
authors: Marziale
authors: Douglas C
authors: DC
authors: Behenna
authors: Scott C
authors: SC
authors: Virgil
authors: Brian M
authors: BM
authors: Stoltz
mesh_terms: D000478:Alkylation; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007769:Lactams; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry
chemical_list: D006571:Heterocyclic Compounds; D007659:Ketones; D007769:Lactams; D010080:Oxazoles; D010720:Phosphines; D010165:Palladium