Catalytic Asymmetric Synthesis of N−N Biaryl Atropisomers

Chemistry - A European Journal, Год журнала: 2023, Номер 30(2)

Опубликована: Окт. 18, 2023

Atropisomers have emerged as important structural scaffolds in natural products, drug design, and asymmetric synthesis. Recently, N-N biaryl atropisomers drawn increasing interest due to their unique structure relatively stable axes. However, its synthesis remains scarce compared well-developed C-C analogs. In this concept, we summarize the of including pyrrole-pyrrole, pyrrole-indole, indole-indole, indole-carbazole, during which a series synthetic strategies are highlighted. Also, evolution is briefly reviewed an outlook offered.

Язык: Английский

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Catalytic Asymmetric α-Functionalization of α-Branched Aldehydes

Molecules, Год журнала: 2023, Номер 28(6), С. 2694 - 2694

Опубликована: Март 16, 2023

Aldehydes constitute a main class of organic compounds widely applied in synthesis. As such, catalyst-controlled enantioselective α-functionalization aldehydes has attracted great interest over the years. In this context, α-branched are especially challenging substrates because reactivity and selectivity issues. Firstly, transient trisubstituted enamines enolates resulting upon treatment with an aminocatalyst or base, respectively, would exhibit attenuated reactivity; secondly, mixtures E- Z-configured enamines/enolates may be formed; third, effective face-discrimination on such sp2 carbon intermediates by incoming electrophilic reagent is not trivial. Despite these issues, last 15 years, several catalytic approaches for prostereogenic that proceed useful yields diastereo- enantioselectivity have been uncovered. Developments include both organocatalytic metal-catalyzed as well dual catalysis strategies forging new carbon–carbon carbon–heteroatom (C-O, N, S, F, Cl, Br, …) bond formation at Cα starting aldehyde. review, some key early contributions to field presented, but focus most recent methods, mainly covering literature from year 2014 onward.

Язык: Английский

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Atroposelective Synthesis of N–N Axially Chiral Bipyrroles via Rhodium-Catalyzed C–H Insertion Reaction

Organic Letters, Год журнала: 2023, Номер 25(26), С. 4808 - 4812

Опубликована: Июнь 27, 2023

An atroposelective synthesis of bipyrroles with an axially chiral N-N bond has been established via a rhodium-catalyzed C-H insertion reaction to provide the desired atropisomers in good yields (up 97% yield) excellent enantioselectivities 99% ee).

Язык: Английский

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Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

Chemical Science, Год журнала: 2023, Номер 14(39), С. 10768 - 10776

Опубликована: Янв. 1, 2023

An important objective in organic synthesis and medicinal chemistry is the capacity to access structurally varied complex molecules rapidly affordably from easily available starting materials. Herein, a protocol for divergent of benzofuran fused azocine derivatives spiro-cyclopentanone benzofurans has been developed via chiral bifunctional urea catalyzed reaction between aurone-derived α,β-unsaturated imine ynone followed by switchable annulation reactions Lewis base catalysts (DBU PPh3) with concomitant epimerization. The skeletally diversified products were formed high yields diastereo- enantioselectivities. Computational analysis DFT accurate DLPNO-CCSD(T) employed gain deeper insights into mechanistic intricacies investigate role skeletal diversity.

Язык: Английский

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Catalytic stereodivergent and simultaneous construction of axial and point chirality

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(12), С. 3308 - 3319

Опубликована: Янв. 1, 2024

An unprecedented ligand-enabled stereodivergent construction of both N–N axial and point chirality in a single step is reported.

Язык: Английский

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