[Show abstract][Hide abstract] ABSTRACT: A novel chiral organic contact ion-pair catalytic system has been developed for the transition-metal-free catalytic enantioselective oxidative cross-dehydrogenative coupling of tertiary amines to ketones for sp3 C–H functionalization. This new strategy provides an efficient and environmentally friendly way to access diversify optically active C1-alkylated tetrahydroisoquinoline derivatives from simple starting materials under mild conditions.
No preview · Article · May 2013 · Chemical Science
[Show abstract][Hide abstract] ABSTRACT: A metal-free intramolecular oxidative cross-coupling reaction for the constructing Csp3Csp3 bonds mediated by 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) under mild conditions was realized for the first time. This novel strategy provides a simple, efficient, and environmentally friendly access to diverse ring-fused tetrahydroquinoline derivatives.
No preview · Article · Mar 2013 · Advanced Synthesis & Catalysis
[Show abstract][Hide abstract] ABSTRACT: The first organocatalytic Michael-cyclization cascade reaction between isothiocyanato oxindoles and unsaturated pyrazolones has been developed. The multicyclic spiro[oxindole/thiobutyrolactam/pyrazolone] core structures containing three contiguous stereogenic centers, including two spiro quaternary centers, were prepared with excellent diastereo- (up to >20 : 1) and enantioselectivities (up to 99% ee).
No preview · Article · Jan 2013 · Chemical Communications
[Show abstract][Hide abstract] ABSTRACT: An organocatalysis/copper-catalyzed asymmetric oxidative sp(3) C-H olefination reaction of tertiary amines with olefins using molecular oxygen as the sole oxidant under mild conditions was realized for the first time. This novel strategy provides an efficient and environmentally friendly way to access diversify optically active C(1)-alkene tetrahydroisoquinoline derivatives.
No preview · Article · Jul 2012 · Journal of the American Chemical Society
[Show abstract][Hide abstract] ABSTRACT: Skeletons in the flask: The first highly enantioselective organocatalytic version of the title reaction using an in situ substrate generation/activation catalytic mode is described. The reaction provides an efficient enantioselective construction of functionalized azaspirocyclic skeletons. The in situ generation of the enolate provides a new way in which to use this important nucleophile in organic synthesis.
No preview · Article · Feb 2012 · Angewandte Chemie International Edition
[Show abstract][Hide abstract] ABSTRACT: Function-oriented design and synthesis of chiral small molecules with novel activity is a key goal in modern organic chemistry. As multiple antibiotic-resistant pathogens are emerging and causing serious diseases, the need for practical routes for the development of new types of antibacterial agents is very urgent. Herein, we present a highly efficient process for the synthesis of optically active pyranocoumarins and 2-amino-4H-chromenes through an organocatalytic Knoevenagel/Michael/cyclization sequence, and the preliminary biological studies of these new heterocyclic compounds revealed potent antibacterial activity. This study provides a novel strategy for further research and development of new types of antibacterial agents effective against human pathogens.
No preview · Article · Dec 2011 · The Journal of Organic Chemistry
[Show abstract][Hide abstract] ABSTRACT: We present herein for the first time the synthesis and preliminary biological evaluation of various modified chromanes via a rosin-derived tertiary amine-thiourea-catalyzed highly enantioselective Friedel-Crafts alkylation reaction.
Full-text · Article · Nov 2011 · Chemical Communications
[Show abstract][Hide abstract] ABSTRACT: We present here the synthesis of dicyano-2-methylenebut-3-enoates as novel Diels-Alder dienes through an efficient PPh(3)-catalyzed strategy, and an unprecedented PPh(3)-catalyzed addition/all-carbon-based asymmetric inverse-electron-demand Diels-Alder sequence reaction is disclosed for the first time.
No preview · Article · Jun 2011 · Chemical Communications