A general procedure for the nucleophilic addition of organozinc halides with nitrones in the presence of trimethylsilyl chloride has been developed. Trimethylsilyl chloride was found to be both an indispensable reaction promoter and a ready hydroxylamine protective agent in these reactions. The produced O-(trimethylsilyl)hydroxylamines can be easily reduced into corresponding amines just by a zinc-copper couple in saturated aqueous NH(4)Cl solution.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c2ob26202a | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Mechanisms of Activating Agents to Form Organozinc Reagents from Zinc Metal: Lessons for Reaction Design.
J Org Chem
January 2025
Department of Chemistry, University of California, Irvine, California 92697-2025, United States.
Activating agents enable the efficient preparation of organozinc complexes from zinc metal and organohalides, but their mechanisms had been obscured by the heterogeneous nature of these systems. Fluorescence microscopy, with the sensitivity to detect surface reaction intermediates, reveals distinct activating mechanisms of widely used activation strategies: trimethylsilyl chloride, LiCl, DMSO, and Rieke zinc powder. The resulting development of mechanistic models provides a better understanding of the oxidative-addition-solubilization sequence in organozinc reagent formation and contains lessons for methods development.
View Article and Find Full Text PDFSynthesis of -Alkyl-1,3-dihydro-2,1-benzisoxazoles.
Org Lett
November 2024
Department of Chemistry, University of Georgia, Athens, Georgia 30602, United States.
We describe a practical method for the synthesis of various substituted -alkyl-1,3-dihydro-2,1-benzisoxazoles and their 2,1-benzisoxazolone precursors starting from readily available methyl 2-nitrobenzoates. The method entails partial nitro reduction with hydrazine and rhodium on carbon to give the hydroxylamines, followed by base-mediated cyclization to give the corresponding benzisoxazol-3(1)-ones. Subsequent alkylation is conducted under basic conditions and is followed by reduction to the target 1,3-dihydrobenzisoxazoles, achieved with lithium aluminum hydride in the presence of trimethylsilyl chloride.
View Article and Find Full Text PDFRapid Synthesis of anti-1,3-Diamino-4-phenylbutan-2-ol Building Blocks via a Three-Component Oxyhomologation and a Two-Component Reducing System.
ChemistryOpen
October 2024
CNRS, ICMMO, CP3A Organic Synthesis Group, Université Paris-Saclay, 17 Avenue des Sciences, 91400, Orsay, France.
N-substituted derivatives of anti-(2R,3S)-1,3-diamino-4-phenylbutan-2-ol are important building blocks for the synthesis of therapeutically important molecules. We describe a simple protocol that allows transformation of N,N-dibenzyl-L-phenylalaninal into such compounds in only two steps. The first step is a fully stereoselective three-component MAC (Masked Acyl Cyanide) oxyhomologation reaction implicating different amines to give a panel of ten N,N-dibenzyl-O-tert-butyldimethylsilyl-protected anti-(2S,3S)-allophenylnorstatin amides.
View Article and Find Full Text PDFInhibition of cytotoxic self-assembly of HEWL through promoting fibrillation by new synthesized α-hydroxycarbamoylphosphinic acids.
RSC Adv
September 2024
Department of Biological Sciences, Institute for Advanced Studies in Basic Sciences (IASBS) Zanjan 45137-66731 Iran
The main objective of the present study is to investigate the potency of new synthesized hydroxycarbamoyl phosphinic acid derivatives in modulating cytotoxic fibrillogenesis of hen egg white lysozyme (HEWL), as a common model in protein aggregation studies. Hydroxycarbamoyl phosphinic acid derivatives were prepared by the reaction of α-hydroxyalkylphosphinic acids with isocyanates (or isothiocyanates) in the presence of trimethylsilyl chloride (TMSCl). The designed process involves the condensation reaction leading to formation of new C sp-P bond formation.
View Article and Find Full Text PDFMechanochemical Synthesis of Chromium(III) Complexes Containing Bidentate PN and Tridentate P-NH-P and P-NH-P' Ligands.
ACS Omega
April 2024
Department of Chemistry, University of Toronto, 80 Saint George Street, Toronto M5S3H6, Ontario, Canada.
Chromium(III) complexes bearing bidentate {NH(CH)PPh: PN, ()-[NH(CHPh)PPh]: P'N} and tridentate [PhP(CH)N(H)(CH)PPh: P-NH-P, ()-(Pr)PCHCHN(H)CH(Ph)CH(Ph)PPh: P-NH-P'] ligands have been synthesized using a mechanochemical approach. The complexes {-[Cr(PN)Cl]Cl (), -[Cr(P'N)Cl]Cl (), -Cr(P-NH-P)Cl (), and -Cr(P-NH-P')Cl ()} were obtained in high yield (95-97%) the grinding of the respective ligands andthe solid Cr(III) ion precursor [CrCl(THF)] with the aid of a pestle and mortar, followed by recrystallization in acetonitrile. The isolated complexes are high spin.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!