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The first enantioselective heteroannulation of 1,3-dienes by 2-iodoanilines and 2-iodobenzylic alcohols is described. The application of a BINOL-derived phosphoramidite ligand bearing electron-withdrawing substituents is the key to obtaining high enantioselectivity. This protocol provides an efficient way to access optically active chiral indolines and isochromans from readily available starting materials.
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http://dx.doi.org/10.1021/acs.joc.6b01611 | DOI Listing |
Org Biomol Chem
September 2024
Key Laboratory of Biotechnology of Antibiotics, Ministry of Health, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences (CAMS) and Peking Union Medical College (PUMC), Beijing 100050, P. R. China.
Adv Sci (Weinh)
July 2024
Shanghai Frontiers Science Center for Drug Target Identification and Delivery, National Key Laboratory of Innovative Immunotherapy, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, 800 Dongchuan Road, Minhang, Sh
The efficient synthesis of chiral 2,2-disubstituted indolin-3-ones is of great importance due to its significant synthetic and biological applications. However, catalytic enantioselective methods for de novo synthesis of such heterocycles remain scarce. Herein, a novel cyclizative rearrangement of readily available anilines and vicinal diketones for the one-step construction of enantioenriched 2,2-disubstituted indolin-3-ones is presented.
View Article and Find Full Text PDFOrg Lett
July 2023
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China.
An organocatalytic atroposelective strategy for the construction of axially chiral compounds containing benzimidazole and quinoline rings is described. The enantioselective heteroannulation reaction of 2-alkynylbenzimidazoles with aminophenylketones proceeded smoothly in the presence of chiral phosphoric acid to provide axially chiral heterobiaryls with good yields and enantioselectivities. This is the first example of the combination of benzimidazole and quinoline rings at the 2- and 3-positions, respectively, into axially chiral heterobiaryls by this new strategy.
View Article and Find Full Text PDFJ Am Chem Soc
May 2021
Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH5304, CH-1015 Lausanne, Switzerland.
Chiral morpholinone is an important building block in organic synthesis and a pharmacophore in medicinal chemistry. However, catalytic enantioselective methods for the construction of this ,-heterocycle remain scarce. We report herein a chiral phosphoric acid-catalyzed enantioselective synthesis of C3-substituted morpholinones from aryl/alkylglyoxals and 2-(arylamino)ethan-1-ols.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2020
Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055, China.
An organocatalytic atroposelective strategy for accessing enantioenriched axially chiral IAN analogues was developed for the first time. A class of novel atropisomeric C2-arylquinoline skeletons were synthesized with high enantiocontrol via chiral phosphoric-acid-catalyzed heteroannulation of in situ generated vinylidene ortho-quinone methide (VQM) intermediates with ortho-aminophenones. The strategy tolerated a broad substrate scope, providing a facile organocatalytic approach to IAN analogues in good yields and excellent enantioselectivities under mild reaction conditions.
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