Chiral amine and polyoxometalate (POM) acids were combined to give highly efficient, stereoselective, and recoverable enamine-based catalysts. Less than 1 mol % of chiral amine loading was sufficient for good catalytic activity, and the catalyst could be recovered and reused 6 times with unchanged enantioselectivity and slightly decreased activity.

Utilizing a late-stage enamine bromofunctionalization strategy, the twelve-step total synthesis of (-)-huperzine Q was accomplished. Furthermore, the first total syntheses of (+)-lycopladines B and C are described. An unprecedented X-ray crystal structure of an unusual epoxyamine intermediate is also reported, and the synthetic application of this intermediate in natural product synthesis is de...

The title salt, C(21)H(27)N(2) (+)·Cl(-) resulted from the condensation between 2,6-dimethyl-aniline and acetyl-acetone in acidified ethanol. The bulky cation is stabilized in a β-imino-enamine tautomeric form, and presents a W-shaped conformation. The benzene rings are arranged almost parallel, with a dihedral angle of 6.58 (4)° between the mean planes. Both N-H groups in the cation form stron...

2-Hydroxydihydropyran-5-ones behave as excellent polyfunctional reagents able to react with enals through oxa-Michael/Michael process cascade under the combination of iminium and enamine catalysis. These racemic hemiacetalic compounds are used as unconventional O-pronucleophiles in the initial oxa-Michael reaction, also leading to the formation of a single stereoisomer under a dynamic kinetic r...

Organocatalyst immobilization onto solid supports represents a promising method for enabling asymmetric organocatalysis while retaining the advantages of heterogeneous catalysts, including catalyst separation, recycling, and use fixed-bed reactors. Understanding how such heterogenized catalytic systems work is fundamental to develop tailor more efficient ones. Herein, we have elucidated role re...

A variety of metabolic deficiencies and human diseases arise from the disruption of mitochondrial enzymes and/or loss of mitochondrial DNA. Mounting evidence shows that eukaryotes have conserved enzymes that prevent the accumulation of reactive metabolites that cause stress inside the mitochondrion. 2-Aminoacrylate is a reactive enamine generated by pyridoxal 5'-phosphate-dependent α,β-eliminas...

Octyl enamine-grafted acetoacetylated polyvinyl alcohol film (AAPVA x –OA) with a “soft-core–hard-sheath” layered structure was prepared through simple soaking. The shows excellent mechanical property and good programmable shape deformation.