Recent Developments in Highly Stereoselective Michael Addition Reactions Catalyzed by Metal Complexes

Abstract

Achieving high enantioselectivity and diastereoselectivity simultaneously­ is a rather challenging task for asymmetric catalytic synthesis­. Thanks to the rapid development of asymmetric transition-metal catalysis, significant progress has been made during recent years in achieving highly enantio- and diastereoselective conjugate addition reactions with a diverse combination of Michael donors and acceptors. This short review surveys the advances in transition-metal-catalyzed asymmetric diastereoselective Michael addition including diastereodivergent catalysis developed between 2015 and 2019. The review is divided into multiple parts according to the type of nucleophiles involved in the reaction.1 Introduction2 Addition of Functionalized Ketones and Dicarbonyl Compounds3 Addition of Aldimino Esters and Their Cyclic Analogues4 Addition of Indolin-2-ones5 Vinylogous Michael Reactions6 Other Michael Donors7 Cascade Reactions Initiated by Michael Addition8 Conclusion

Stereoselective Promiscuous Reactions Catalyzed by Lipases

“…The 1,4-additions of different nucleophiles to activated olefins are grouped as Michael reactions and represent a versatile method for the construction of C-C or C-X bonds. The olefin component (Michael acceptor) is in most cases an α,β-unsaturated carbonyl compound, but nitroolefins, maleimides, acrylonitrile, and acrylate derivatives also undergo the nucleophilic addition of enolates, amines, thiols, and phosphines (Michael donors) in the presence of a variety of organocatalysts, metal-based or Lewis acid catalysts [ 33 , 34 ].…”

Divergent and Diastereoselective Synthesis of α-Monosubstituted and trans-α,β-Disubstituted γ-Lactams from (S)-N,N-Dibenzyl-α-amino Aldehydes via Henry and Michael Reactions

“…Chiral N,N-dibenzylated -aminated nitroalkenes and chiral N,N-dibenzylated -aminated aldehydes are obtained from natural L-amino acids and have been utilized as versatile electrophilic chirons that induct high grade of 1,2-diastereoselection in diverse diastereoselective syntheses of versatile synthetic intermediates. Asymmetric or racemic Henry reaction [16][17][18][19][20][21][22][23] and Michael addition [24][25][26][27][28][29][30] are two of the most important reactions used to form C-C bonds. They are generally very easy to perform, are catalyzed by a large number of different basic homogeneous or heterogeneous systems and occur at room temperature in the presence of different organic solvents, water or without solvent.…”

Exploring the copper binding ability of Mets7 hCtr‐1 protein domain and His7 derivative: An insight in Michael addition catalysis

“…This replacement allowed Cu (II) binding, 38,39 with the obtainment of a stable turn conformation as evicted by CD experiments. In Michael addition, 40 His7‐Cu (II) proved to be a better catalyst than Mets7‐Cu(I) . In particular, when the substrate was the ( E )‐1‐phenyl‐3‐(pyridin‐2‐yl)prop‐2‐en‐1‐one, a conversion of 71% and a significant 58% of e.e.…”