An asymmetric Michael reaction between cyclopentane-1,2-dione and alkylidene oxindole was studied in the presence of a multifunctional squaramide catalyst. Michael adducts were obtained in high enantioselectivities and in moderate diastereoselectivities.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8822468 | PMC |
http://dx.doi.org/10.3762/bjoc.18.18 | DOI Listing |
Org Lett
January 2025
Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.
1,1-Difluoroallenes underwent regioselective [2 + 2] and [3 + 2] cycloadditions with aldehydes using Au(I) catalysts. An AuCl catalyst enabled an α,β-selective [2 + 2] cycloaddition of 1,1-difluoroallenes, yielding ()-3-alkylidene-2,2-difluorooxetanes. Conversely, an AuCl(IPr)-AgSbF catalyst facilitated an α,γ-selective [3 + 2] cycloaddition, followed by dehydrofluorination to produce aromatized 2-fluorofurans.
View Article and Find Full Text PDFCurr Org Synth
January 2025
Laboratoire de Chimie Organique (LR17ES08), Faculté des Sciences de Sfax, University of Sfax, Route de Soukra Km 3.5, BP 1171, 3000, Sfax, Tunisia.
Aim And Objective: It is well established that 4H-pyran derivatives hold a significant position in synthetic organic chemistry due to their diverse biological and pharmacological properties. This work aims to introduce a novel synthetic pathway for highly functionalized 4H-pyran derivatives, achieved through a 1,4-Michael addition followed by a cascade cyclization. This reaction is catalyzed by LiOH·H2O under ultrasonic irradiation in water, offering an efficient and environmentally friendly approach.
View Article and Find Full Text PDFInorg Chem
January 2025
University of Göttingen, Institute of Inorganic Chemistry, Tammannstrasse 4, D-37077 Göttingen, Germany.
Alkyl nickel intermediates relevant to catalytic processes often feature agostic stabilization, but relatively little is known about the situation in oligonickel systems. The dinickel(I) complex K[LNi], which is based on a compartmental pyrazolato-bridged ligand L with two β-diketiminato chelate arms, or its masked version, the dihydride complex [KL(Ni-H)] that readily releases H, oxidatively add methyl tosylate to give diamagnetic [LNi(CH)] () with (Ni···Ni) ≈ 3.7 Å.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
School of Chemistry, Dalian University of Technology, Dalian, 116024, P. R. China.
The Pd-catalyzed asymmetric hydrogenolysis rearrangement of allylic acetates using (s-Bu)BHK has been described, achieving the synthesis of axially chiral alkylidene cycloalkanes with excellent enantioselectivities (up to 99 % ee) and a wide substrate scope (30 examples of cyclohexanes and cyclobutanes). To the best of our knowledge, this is the first time to achieve synthesis of axially chiral olefins via asymmetric hydrogenolysis of allylic acetates. This methodology not only offers a novel synthetic pathway for non-atropisomeric axially chiral structures but also highlights the potential of asymmetric hydrogenolysis as a powerful tool in synthetic organic chemistry.
View Article and Find Full Text PDFOrganometallics
December 2024
Department of Chemistry, University of York, Heslington, York YO10 5DD, U.K.
stabilization of known, but solution unstable, methylidene complex [Ir(Bu-PONOP)(=CH)][BAr ] allows single-crystal to single-crystal solid/gas reactivity associated with the {Ir=CH} group to be studied. Addition of H results in [Ir(Bu-PONOP)(H)][BAr ]; exposure to CO forms iridium(I) carbonyl [Ir(Bu-PONOP)(CO)][BAr ], and reaction with NH gas results in the formation of methylamine complex [(Bu-PONOP)Ir(NHMe)][BAr ] via an aminocarbene intermediate. Periodic density functional theory and electronic structure analyses confirm the Ir=CH bond character but with a very low barrier to rotation around the Ir=CH bond.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!