An efficient enantioselective synthesis of cyclic α-aminophosphonates via multicomponent reactions of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate has been developed with the use of a chiral silver spirocyclic phosphate as the catalyst. This protocol provides straightforward access to a series of chiral C1-phosphonylated 1,2-dihydroisoquinoline derivatives with high yields (up to 99%) and high enantioselectivities (up to 94% ee) for a broad substrate scope. The products could be further transformed into densely functionalized compounds and corresponding α-aminophosphonic acids.
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http://dx.doi.org/10.1021/acs.orglett.0c02487 | DOI Listing |
Molecules
November 2022
Faculty of Science, Kunming University of Science and Technology, South Jingming Road 727, Chenggong District, Kunming 650500, China.
An operationally simple Ag(I)-catalyzed approach for the synthesis of isoquinoline and quinazoline fused 1,2,3-triazoles was developed by a condensation and amination cyclization cascade of amino--1,2,3-triazoles with 2-alkynylbenzaldehydes involving three new - bond formations in one manipulation, in which the group of - of the triazole ring serves as a nucleophile to form the quinazoline skeleton. The efficient protocol can be applied to a variety of substrates containing a range of functional groups, delivering novel pentacyclic fused 1,2,3-triazoles in good-to-excellent yields.
View Article and Find Full Text PDFOrg Lett
November 2020
Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
An efficient synthesis of 1,2,3,4-tetrahydrobenzo[]quinoline derivatives through PdCl-catalyzed, TBHP-promoted, and toluene-mediated dehydrogenation/[4+2] cycloaddition of saturated cyclic amines with 2-alkynylbenzaldehydes was developed. On the contrary, when the reaction medium was changed from toluene to DMSO/HO, another class of important compounds, naphthyl chain amines, formed via a dehydrogenation-intermolecular condensation-C-N bond cleavage-intramolecular condensation pathway, was obtained with good selectivity.
View Article and Find Full Text PDFOrg Lett
September 2020
Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
An efficient enantioselective synthesis of cyclic α-aminophosphonates via multicomponent reactions of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate has been developed with the use of a chiral silver spirocyclic phosphate as the catalyst. This protocol provides straightforward access to a series of chiral C1-phosphonylated 1,2-dihydroisoquinoline derivatives with high yields (up to 99%) and high enantioselectivities (up to 94% ee) for a broad substrate scope. The products could be further transformed into densely functionalized compounds and corresponding α-aminophosphonic acids.
View Article and Find Full Text PDFOrg Lett
September 2015
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 135 Xingang West Road, Guangzhou 510275, China.
Diazo compounds have been employed as the nucleophile in a silver-catalyzed three-component reaction with amines and 2-alkynylbenzaldehydes. Various 3-benzazepines were prepared in a one-pot manner based on a cascade imine--yne cyclization/nucleophilic addition/1,2-aryl migration process. Moreover, this Ag(I)-mediated reaction also provides a practical route to diazo-containing dihydroisoquinolines under slightly modified conditions.
View Article and Find Full Text PDFChem Commun (Camb)
August 2012
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
A method for synthesis of 4-bromoisoquinolones has been developed starting from 2-alkynylbenzaldehydes and primary amines mediated by CuBr under an O(2) atmosphere, where CuBr plays multiple roles to facilitate the present reactions.
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