Direct Asymmetric Amination of α-Branched Cyclic Ketones Catalyzed by a Chiral Phosphoric Acid
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چکیده
منابع مشابه
Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid.
Here we report the direct asymmetric amination of α-substituted cyclic ketones catalyzed by a chiral phosphoric acid, yielding products with a N-containing quaternary stereocenter in high yields and excellent enantioselectivities. Kinetic resolution of the starting ketone was also found to occur on some of the substrates under milder conditions, providing enantioenriched α-branched ketones, ano...
متن کاملAsymmetric reduction of ketones by phosphoric acid derived catalysts.
Enantioenriched secondary alcohols represent an important class of molecules found in numerous intermediates, chiral building blocks, and biologically active compounds. Asymmetric reduction of prochiral ketones constitutes the most straightforward way to form these important moieties. Traditionally, stoichiometric amounts of chiral ligands were used together with an aluminium or a boron hydride...
متن کاملAsymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c5sc04202j Click here for additional data file.
We describe the asymmetric addition of unactivated α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid, generating an all-carbon quaternary stereocenter with broad substrate scope and high enantioselectivity. The products are easily transformed into their corresponding 1,5- and 1,4-ketoaldehyde derivatives, which are both important building blocks in organic synthesis.
متن کاملChiral phosphoric acid catalyzed asymmetric transfer hydrogenation of quinolines in a sustainable solvent
The use of diethyl carbonate as a sustainable solvent for organocatalytic asymmetric transfer hydrogenations of 2-substituted quinolines using highly efficient chiral phosphoric acid catalysts with Hantzsch esters as a hydrogen source is reported for the first time. The asymmetric transfer hydrogenation reaction in diethyl carbonate provides enantiomerically pure 1,2,3,4-tetrahydroquinolines wi...
متن کاملThe first catalytic asymmetric thioacetalization by chiral phosphoric acid catalysis.
We report here the first catalytic asymmetric thioacetalization of salicylaldehyde and dithiol. Chiral phosphoric acid STRIP C5 is identified as a powerful catalyst for this reaction to afford various chiral dithioacetals in high to excellent yields and enantioselectivities under mild conditions.
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2015
ISSN: 0002-7863,1520-5126
DOI: 10.1021/jacs.5b00229