Cobalt-catalyzed asymmetric phospha-Michael reaction of diarylphosphine oxides for the synthesis of chiral organophosphorus compounds

Abstract

The asymmetric Michael addition of phosphorus nucleophiles to electron-deficient alkenes is one of the most direct and atom-economical methods to provide chiral organophosphorus compounds with high efficiency in recent years....

Enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated ketones catalyzed by oxazaborolidines

“…30,31 Moreover, Ni and Co catalysts can also lead to excellent results in asymmetric hydrophosphination. [32][33][34] In addition, lots of other metals could also catalyze the enantioselective phospha-Michael addition reactions by serving as chiral Lewis acids to activate unsaturated substrates, such as Al, Zn, Mg, Ti, Yb, Re etc. [35][36][37][38] However, considering the generation of chiral C-P scaffolds, they usually can coordinate with metal catalysts and thus cause catalyst poisoning.…”

“…30,31 Moreover, Ni and Co catalysts can also lead to excellent results in asymmetric hydrophosphination. 32–34 In addition, lots of other metals could also catalyze the enantioselective phospha-Michael addition reactions by serving as chiral Lewis acids to activate unsaturated substrates, such as Al, Zn, Mg, Ti, Yb, Re etc . 35–38…”

Visible-light-mediated α-amino alkylation of ketimines and aldimines for the synthesis of 1,2-diamines

“…spermine 3 and (−)-agelastatin A 4 ) and antiviral drugs (e.g. Tamiflu 5 ), and as auxiliary ligands 6 and as chiral catalysts 7,8 in asymmetric synthesis. The synthesis of 1,2-diamines has attracted much attention in synthetic chemistry, and several methods have been reported such as the classical representative Mannich reactions.…”

Application of Oxazaborolidine Catalysts (CBS) on Enantioselective 1,4-Addition of Diarylphosphine Oxides to α,β-Unsaturated Thioesters

“…For example, in 2010, Duan and co-workers disclosed the first palladium-catalyzed asymmetric addition of diarylphosphines to enones by using a chiral pincer ligand . Subsequently, various transition metals, including Ni, Cu, Mn, and Co, were employed with chiral ligands to construct a wide range of chiral phosphorus-based molecules described by the groups of Leung, Wang, Yin, and Harutyunyan . In addition, several metals, such as Al, Zn, Mg, Ti, Yb, and Re, could also work as chiral Lewis acids by activating unsaturated substrates to catalyze asymmetric phospha-Michael addition reactions …”