Organocatalytic enantioselective conjugate addition of 2-naphthols to ortho-hydroxyphenyl substituted para-quinone methides: access to unsymmetrical triarylmethanes
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Asymmetric Conjugate Addition of ortho-Quinone Methides as a Pathway to the Core of Nomofungin
Asymmetric Conjugate Addition of ortho-Quinone Methides as a Pathway to the Core of Nomofungin Introduction: Tetracyclic structures are found at the core of many biologically active molecules. One class of compounds with a tetracyclic core is the family of communesin products. 1 These products have shown cytotoxicity against several leukemia cell lines as well as insecticidal activity against s...
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Presented is the first enantioselective copper-catalyzed 1,6-conjugate addition of bis(pinacolato)diboron to para-quinone methides. The reaction proceeds with excellent yields and good to excellent enantioselectivities, and provides an attractive approach to the construction of optically active gem-diarylmehtine boronic esters. Additionally, the subsequent conversion of the derived potassium tr...
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The first enantioselective organocatalytic amine conjugate addition has been successfully developed. The application of LUMO-lowering iminium catalysis has enabled the highly chemo- and enantioselective 1,4-addition of a rationally designed N-silyloxycarbamate nucleophile (HOMO-raised) to alpha,beta-unsaturated aldehydes. Imidazolidinone 2*pTSA was found to catalyze the addition of various orth...
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An organocatalytic conjugate addition of prochiral 3-fluorinated oxindoles to vinyl sulfones was described for the first time. In the presence of bifunctional tertiary amine-thiourea catalysts, 3-fluoro-3-substituted oxindole adducts were obtained in excellent yields and with high enantiomeric excesses.
متن کاملEnantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides
The use of Cinchona alkaloid-based chiral ammonium ylides allows for the first highly enantioselective and broadly applicable spirocyclopropanation reactions of para-quinone methides. This strategy provides a straightforward protocol toward the chiral spiro[2.5]octa-4,7-dien-6-one skeleton, which is a frequently found structural motif in important biologically active molecules.
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ژورنال
عنوان ژورنال: RSC Advances
سال: 2019
ISSN: 2046-2069
DOI: 10.1039/c9ra04768a