Dynamic Kinetic Asymmetric Transformation (DYKAT) by Combined Amine‐ and Transition‐Metal‐Catalyzed Enantioselective Cycloisomerization

Abstract

The first examples of one-pot highly chemo- and enantioselective dynamic kinetic asymmetric transformations (DYKATs) involving alpha,beta-unsaturated aldehydes and propargylated carbon acids are presented. These DYKATs, which proceed by a combination of catalytic iminium activation, enamine activation, and Pd(0)-catalyzed enyne cycloisomerization, give access to functionalized cyclopentenes with up to 99 % ee and can be used for the generation of all-carbon quaternary stereocenters.

Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations

“…The Cordova group has since expanded this technology to obtain a variety of useful structural motifs. 238,239 …”

Combined heterogeneous metal/organic catalysts for eco-friendly synthesis

“…Different Pd(0)-catalysts were used for the ARC [48,57,68]. Here the catalysts systems with Pd(0)-AmP-MCF or Pd(0)-aminopropyl-controlled pore glass (Pd(0)-AmP-CPG) as the co-catalyst exhibited a broad substrate scope and delivered various carbocycles 10, heterocycles 11 and 12 with high ers [69][70][71]. Here Pd(0)-AmP-CPG was the most efficient co-catalyst for this relay sequence.…”

The Marriage of Organocatalysis with Metal Catalysis: Access to Multisubstituted Chiral 2,5‐Dihydropyrroles by Cascade Iminium/Enamine–Metal Cooperative Catalysis

“…[4][5] Despite its advantages, the number of cooperative catalysis reactions that have been developed is by far less than those in which a single catalyst is employed. One major factor that contributes to this disparity is the incompatibility between transition metals and organocatalysts.…”