Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates
TLDR
High stereoselective carbolithiation reactions of α-aryl piperidine enecarbamates that offer direct access to vicinally-substituted piperidines and it is demonstrated that the carbanion intermediates can be trapped with a carbon electrophile.About:
This article is published in Chemical Communications.The article was published on 2015-04-21 and is currently open access. It has received 17 citations till now. The article focuses on the topics: Piperidine & Nucleophile.read more
Citations
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trans-Selective Aryldifluoroalkylation of Endocyclic Enecarbamates and Enamides by Nickel Catalysis
TL;DR: This protocol paves a new way to the efficient synthesis of functionalized azetidines that are of great interest in pharmacological studies, providing a straightforward and efficient access to an array of pyrrolidine- and azetidine-containing fluorinated amino acids and oligopeptides, which may have applications in life science.
Journal ArticleDOI
One-pot fabrication of FRET-based fluorescent probe for detecting copper ion and sulfide anion in 100% aqueous media.
TL;DR: The FRET-based probe PF may provide a new method for selective detection of multifarious analysts in biological and environmental applications, and even hold promise for application in more complicated systems.
Journal ArticleDOI
Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides
Hannah Braunstein,Spencer Langevin,Monique Khim,Jonathan Adamson,Katie Hovenkotter,Lindsey Kotlarz,Brandon Mansker,Timothy K. Beng +7 more
TL;DR: A modular substrate-controlled hexannulation of inherently promiscuous 1,3-azadienes with Hexacyclic anhydrides with hexacyclics affords versatile vicinally functionalized allylic lactams, in high yields, regio- and stereoselectivities is described.
Journal ArticleDOI
Regiocontrolled synthesis of (hetero)aryl and alkenyl dehydropyrrolidines, dehydropiperidines and azepenes by Ru-catalyzed, heteroatom-directed α-C-H activation/cross-coupling of cyclic enamides with boronic acids.
TL;DR: The synthesis of α-aryl and alkenyl pyrrolidine-, piperidine-, and azepane derivatives, through the intermediacy of cyclic enamides is described, and regioselectivity is governed by the rate differences between sp(2) and sp(3) C-H activation and the necessity for chelation between the ruthenium metal and the carbonyl directing group.
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One-shot access to α,β-difunctionalized azepenes and dehydropiperidines by reductive cross-coupling of α-selenonyl-β-selenyl enamides with organic bromides
TL;DR: The synthesis of α- and α,β-functionalized azepenes and dehydropiperidines from readily prepared α-selenonyl eneformamides or enecarbamates has been achieved through Fe-catalyzed α-substitutive deselenonation, β-regioselective lithiation/trapping, and Co-Catalyzed reductive cross-coupling protocols.
References
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TL;DR: There are six principal methods of umpolung: 1 2n-oxidation, heteroatom exchange and modification, homologation and its reversal, the cyclopropane “trick”, use of acetylenes, and redox reactions; under certain circumstances none of these techniques is necessary in cases where direct umpoline is possible.
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TL;DR: A method for the diastereoselective synthesis of 2,4-disubstituted piperidines has been developed which enables the complete control of reaction selectivity merely by changing the order of the reaction sequence.
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Asymmetric routes to substituted piperidines
TL;DR: An overview of the main asymmetric routes to substituted piperidines is presented in this paper, which concentrates on general methodologies that provide enantioselective routes to piperidine derivatives.