Role of Cinchona Alkaloids in the Enantio- and Diastereoselective Synthesis of Axially Chiral Compounds
Sign Up to like & getrecommendations! Published in 2022 at "Accounts of Chemical Research"
DOI: 10.1021/acs.accounts.2c00515
Abstract: Conspectus Asymmetric synthesis using organic catalysts has evolved since it was first realized and defined. Nowadays, it can be considered a valid alternative to transition metal catalysis for synthesizing chiral molecules. According to the literature,… read more here.
Keywords: role cinchona; cinchona alkaloids; synthesis; desymmetrization ... See more keywords
Phosphine-Catalyzed Atroposelective Formal [3 + 2] Cycloaddition Desymmetrization of N-Arylmaleimides.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02208
Abstract: Herein, a new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was devised by [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This desymmetrization process allows for quick… read more here.
Keywords: phosphine catalyzed; cycloaddition desymmetrization; atroposelective formal; formal cycloaddition ... See more keywords
CuH-Catalyzed Enantioselective Desymmetrization of Cyclic 1,3-Diketones.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c03359
Abstract: Herein, we report a CuH-catalyzed asymmetric desymmetrization of prochiral cyclopentane-1,3-diones to access cyclic 3-hydroxy ketones having an all-carbon quaternary center with high diastereoselectivity via hydrosilylation using PMHS as an inexpensive hydride source. This reaction displays… read more here.
Keywords: cuh catalyzed; desymmetrization cyclic; desymmetrization; enantioselective desymmetrization ... See more keywords
Enantioselective Michael Addition/Cyclization/Desymmetrization Sequence of Prochiral Cyclic Hemiacetals and Nitroolefins: Synthesis of Chiral Oxygen-Bridged Bicyclic Compounds.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c03815
Abstract: The organocatalytic enantioselective Michael addition of functionalized prochiral cyclic hemiacetals and nitroolefins has been developed under cooperative enamine and hydrogen bond catalysis. The obtained chiral hemiacetal intermediates could be used in the subsequent diastereocontrolled cyclization/desymmetrization… read more here.
Keywords: michael addition; prochiral cyclic; enantioselective michael; cyclic hemiacetals ... See more keywords
Isothiourea-Catalyzed Acylative Desymmetrization of Silicon-Centered Bisphenols.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c00946
Abstract: The preparation of optically pure organosilicon compounds bearing a stereogenic center at the silicon atom is an attractive but challenging enterprise. Herein we disclose an isothiourea (ITU)-catalyzed monoacylation reaction of silicon-centered bisphenols with 2,2-diphenylacetic pivalic… read more here.
Keywords: catalyzed acylative; isothiourea catalyzed; silicon centered; desymmetrization ... See more keywords
Highly Enantioselective Desymmetrization of Centrosymmetric pseudo-para-Diformyl[2.2]paracyclophane via Asymmetric Transfer Hydrogenation
Sign Up to like & getrecommendations! Published in 2018 at "ACS Catalysis"
DOI: 10.1021/acscatal.8b01872
Abstract: Herein we describe the desymmetrization of a centrosymmetric pseudo-para-diformyl[2.2]paracyclophane based on Noyori asymmetric transfer hydrogenations (ATH). The reduction proceeds smoothly in the presence of commercially available ruthenium complexes to afford a monohydroxymethylated product in good… read more here.
Keywords: pseudo para; desymmetrization centrosymmetric; para diformyl; centrosymmetric pseudo ... See more keywords
Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning.
Sign Up to like & getrecommendations! Published in 2021 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.1c00759
Abstract: Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral… read more here.
Keywords: enantioselective desymmetrization; desymmetrization aryl; aryl propanediols; catalyst ... See more keywords
Desymmetrization via Activated Esters Enables Rapid Synthesis of Multifunctional Benzene-1,3,5-tricarboxamides and Creation of Supramolecular Hydrogelators
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.1c12685
Abstract: Supramolecular materials based on the self-assembly of benzene-1,3,5-tricarboxamide (BTA) offer an approach to mimic fibrous self-assembled proteins found in numerous natural systems. Yet, synthetic methods to rapidly build complexity, scalability, and multifunctionality into BTA-based materials… read more here.
Keywords: rapid synthesis; benzene; bta; desymmetrization ... See more keywords
Reactivity Enhancement of a Zerovalent Diboron Compound by Desymmetrization.
Sign Up to like & getrecommendations! Published in 2018 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.8b06930
Abstract: The desymmetrization of the cyclic (alkyl)(amino)carbene-supported diboracumulene B2(cAACMe)2 (cAACMe = 1-(2,6-diisopropylphenyl)-3,3,5,5-tetramethylpyrrolidin-2-ylidene) by monoadduct formation with IMeMe (1,3-dimethylimidazol-2-ylidene) yields the zerovalent sp-sp2 diboron compound B2(cAACMe)2(IMeMe), which provides a versatile platform for the synthesis of novel symmetrical… read more here.
Keywords: imeme; diboron; diboron compound; zerovalent ... See more keywords
Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones.
Sign Up to like & getrecommendations! Published in 2019 at "Chemical communications"
DOI: 10.1039/c8cc08985j
Abstract: The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19 : 1… read more here.
Keywords: construction dihydrobenzofuran; dihydrobenzofuran dione; desymmetrization quinols; asymmetric construction ... See more keywords
Oxidative Desymmetrization of Isoindolines Realized by tert-Butyl Nitrite (TBN) Initiated Radical sp3 C–H Activation Relay (CHAR)
Sign Up to like & getrecommendations! Published in 2021 at "Synthesis"
DOI: 10.1055/s-0040-1706010
Abstract: An oxidative desymmetrization of isoindolines was realized by TBN initiated radical sp3 C–H activation relay (CHAR), providing a series of ω-hydroxylactams in high yields. This reaction exhibits broad substrate scope and functional group tolerance, and… read more here.
Keywords: initiated radical; desymmetrization isoindolines; oxidative desymmetrization; desymmetrization ... See more keywords