Chiral dihydroxytetraphenylene-catalyzed enantioselective conjugate addition of boronic acids to β-enaminones

Abstract

We report the (S)-2,15-Cl2-DHTP-catalyzed enantioselective conjugate addition of organic boronic acids to β-enaminones, providing the corresponding addition products in high yields and moderate to excellent enantioselectivities (up to 98% ee)....

Iridium-catalyzed enantioselective alkynylation and kinetic resolution of alkyl allylic alcohols

“…9 Amongst these tetraphenylene-based asymmetric catalysts, enantioenriched 1,16-dihydroxytetraphenylene ( DHTP ) stands out. 9 f – h ,10 More recently, our group developed a series of phosphoramidite ligands based on the ( S )- DHTP framework, of which the ( S )- DHTP derived (phosphoramidite, olefin) ligand ( S )- L1 exhibited excellent efficiency in the iridium-catalyzed asymmetric allylic alkynylation of allylic alcohols. 9 h This Ir/( S )- L1 -catalyzed asymmetric allylic alkynylation led to the formation of a variety of 1,4-enynes with high regio- and enantioselectivities.…”

Enantioselective Organocatalytic Conjugate Addition in a Tandem Synthesis of δ-Substituted Cyclohexenones and Four-Step Total Synthesis of Penienone

“…Recently, our group developed a conjugate addition/elimination cascade reaction in a unique use of vinylogous esters as conjugate acceptors . The Mao and Chang groups shortly thereafter reported the enantioselective 1,4-conjugate addition on a vinylogous amide to synthesize the corresponding amine . In this report, we extend the vinylogous system by an additional alkenyl unit, with the corresponding doubly vinylogous ester being easily generated by nucleophilic addition to a terminal alkyne.…”