Synergistic diselenide/guanidine catalyzed dehydrophosphorylation of 2-nitrobenzhydrols to access C-stereogenic
Jin-Yu Gong1, Pan-Pan Zhou1, Yu-Hao Qiao1
1State Key Laboratory of Natural Product Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University 222 South Tianshui Road Lanzhou 730000 China yangshd@lzu.edu.cn.
Abstract:
The development of a catalytic and mild variant of the Atherton-Todd reaction for the synthesis of chiral phosphorus-containing compounds presents substantial challenges. Herein, we report a method for accessing C-stereogenic phosphinates enabled by a synergistic diselenide/chiral guanidine catalytic system. This method avoids stoichiometric halogenating reagents, generating water as the sole byproduct. Mechanistic studies reveal that the electron-deficient diselenide catalyst serves as a recyclable alternative for halogenating agents, while the chiral guanidine activates the alcohol via Brønsted base catalysis. This strategy effectively achieves the kinetic resolution of secondary alcohols with similar steric substituents, offering a sustainable strategy to access phosphinates with stereogenic benzhydryl groups.
More Related Videos
09:45Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
Sharpless Epoxidation
Preparation of Nitriles
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Preparation and Reactions of Sulfides
