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A highly efficient enantioselective nitroso Diels-Alder reaction of 6-methyl-2-nitroso pyridine with various 1,3-dienes was successfully developed using a Cu(i)/(S)-TF-BiphamPhos complex as the catalyst. For most of the cyclic dienes, synthetically important heterocyclic 3,6-dihydro-1,2-oxazines were obtained in high yields with excellent regio-, diastereo- and enantioselectivities. Acyclic 2-silyloxy-1,3-diene also worked well in the reaction.
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http://dx.doi.org/10.1039/c6cc09587a | DOI Listing |
Org Lett
September 2024
Department of Chemistry and Biochemistry, Baylor University, One Bear Place 97348, Waco, Texas 76798, United States.
Herein we describe a total synthesis of the heterodimeric securinega alkaloid (-)-flueggeacosine C (). The convergent synthetic strategy is based on a Liebeskind-Srogl cross-coupling reaction that combines a benzoquinolizidine fragment with a securinine-type alkaloid. An acyloxy nitroso ring-expansion was employed as the key step in accessing benzoquinolizidine , and a novel intramolecular Diels-Alder reaction of an allenic acid-containing pyridone expeditiously delivers the skeleton of the securinine-type fragment ().
View Article and Find Full Text PDFOrg Lett
April 2024
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Cranomycin and jogyamycin, two aminocyclopentitol natural products, possess complex structures and potential medicinal properties. This review describes synthetic studies about the process of making an advanced intermediate of cranomycin and jogyamycin. This highly functionalized intermediate, featuring three contiguous amine-substituted stereocenters, was constructed from cyclopentadiene through a series of reactions including the nitroso Diels-Alder reaction, nitrogen radical cyclization reaction, 1,2-nitrogen migration, and stereoselective nitrogen addition.
View Article and Find Full Text PDFJ Am Chem Soc
December 2023
Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, Gif-sur-Yvette Cedex 91198, France.
Conjugated trienes are fascinating building blocks for the rapid construction of complex polycyclic compounds. However, limited success has been achieved due to the challenging regioselectivity control. Herein, we report an enantio- and diastereoselective process allowing to regioselectively control the functionalization of H-triene-carbamates.
View Article and Find Full Text PDFJ Mol Graph Model
December 2023
Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran.
Density functional theory calculations at the M06-2X/aug-cc-pVTZ level of theory have been used to examine the Nitroso-Diels-Alder (N-D-A) cycloaddition reaction between the CHN=O and cis-1,3-butadiene in the presence of POX (X=F, Cl, OH) as a catalyst. The effect of the above POX compounds on the activation energy of the N-D-A reaction, has been studied here. In the first stage, the energies of two different bonding interactions, via P⋯N versus P⋯O binding, between the POX and CHN=O molecules were calculated.
View Article and Find Full Text PDFThe formation of new carbon-nitrogen bonds is indisputably one of the most important tasks in synthetic organic chemistry. Here, nitroso compounds offer a highly interesting reactivity that complements traditional amination strategies, allowing for the introduction of nitrogen functionalities ene-type reactions or Diels-Alder cycloadditions. In this study, we highlight the potential of horseradish peroxidase as biological mediator for the generation of reactive nitroso species under environmentally benign conditions.
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