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Author

Thomas Varlet

Bio: Thomas Varlet is an academic researcher from Institut de Chimie des Substances Naturelles. The author has contributed to research in topics: Enantioselective synthesis & Chemistry. The author has an hindex of 3, co-authored 6 publications receiving 25 citations.

Papers
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Journal ArticleDOI
TL;DR: In this paper, an efficient enantioselective construction of tetrahydronaphthalene-1,4-diones as well as dihydronaphthalene 1,4diols by a chiral phosphoric acid catalyzed quinone Diels-Alder reaction with dienecarbamates is reported.
Abstract: An efficient enantioselective construction of tetrahydronaphthalene-1,4-diones as well as dihydronaphthalene-1,4-diols by a chiral phosphoric acid catalyzed quinone Diels-Alder reaction with dienecarbamates is reported. The nature of the protecting group on the diene is key to the success of achieving high enantioselectivity. The divergent "redox" selectivity is controlled by using an adequate amount of quinones. Reversible redox switching without erosion of enantioselectivity was possible from individual redox isomers.

24 citations

Journal ArticleDOI
TL;DR: The remarkable versatility of these cycloadditions to access chiral cyclic amines with different ring sizes ranging from 5- to 7-membered rings is showcased, with an emphasis on biologically active natural products.

19 citations

Journal ArticleDOI
TL;DR: In this paper, a diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates.
Abstract: A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to our previous work dealing with enecarbamates.

18 citations

Journal ArticleDOI
TL;DR: A novel practical, catalyst-free, azo-Diels-Alder reaction between dienecarbamates and azodicarboxylates exhibiting a remarkable functional group tolerance makes this cycloaddition a viable supplement to the other reactions in "click" chemistry.

5 citations


Cited by
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Journal ArticleDOI
TL;DR: In this article, a profound revision on the latest advances on the organocatalytic asymmetric inverse-electron demand hetero-Diels-Alder reaction is shown.
Abstract: Cycloaddition reactions, in particular Diels-Alder reactions, have attracted a lot of attention from organic chemists since they represent one of the most powerful methodologies for the construction of carbon-carbon bonds. In particular, inverse-electron-demand hetero-Diels-Alder reactions have been an important breakthrough for the synthesis of heterocyclic compounds. Among all their variants, the organocatalytic enantioselective version has been widely explored since the asymmetric construction of diversely functionalized scaffolds under reaction conditions encompassed within the green chemistry field is of great interest. In this review, a profound revision on the latest advances on the organocatalytic asymmetric inverse-electron demand hetero-Diels-Alder reaction is shown.

20 citations

Journal ArticleDOI
TL;DR: The remarkable versatility of these cycloadditions to access chiral cyclic amines with different ring sizes ranging from 5- to 7-membered rings is showcased, with an emphasis on biologically active natural products.

19 citations

Journal ArticleDOI
TL;DR: In this paper, a diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates.
Abstract: A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to our previous work dealing with enecarbamates.

18 citations

Journal ArticleDOI
TL;DR: The first enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines was realized using a chiral phosphoric acid as catalyst.

16 citations

Journal ArticleDOI
TL;DR: This review summarizes recent developments in the area of Brønsted acid-catalyzed, enantioselective cycloadditions of ortho-quinone methide imines as well as heterocyclic indole- and pyrrol-based methides.
Abstract: This review summarizes recent developments in the area of Brønsted acid-catalyzed, enantioselective cycloadditions of ortho-quinone methides, ortho-quinone methide imines as well as heterocyclic indole- and pyrrol-based methides. In a straightforward and single-step transformation complex polycyclic N- and O-heterocyclic scaffolds are accessible with typically good yields and excellent stereocontrol from simple benzyl and heterobenzyl alcohols upon acid-catalyzed dehydration. The transient precursors are hydrogen-bonded to a chiral Brønsted acid which controls the enantioselectivity of the process.

16 citations