Aza‐Ortho‐Quinone Methides as Reactive Intermediates: Generation and Utility in Contemporary Asymmetric Synthesis DOI
Hsuan‐Hung Liao, Shinje Miñoza, Shao‐Chi Lee

и другие.

Chemistry - A European Journal, Год журнала: 2022, Номер 28(46)

Опубликована: Июнь 2, 2022

Abstract The aza‐ ortho ‐quinone methide (aza‐ o ‐QM) chemistry has overwhelmingly progressed in the past few decades. This review aims to integrate various transition metal‐catalyzed and organocatalytic strategies taming aza ‐o‐ QM intermediates, including ‐vinylidene quinone ‐VQM), ‐alkynyl ‐AQM), para p ‐QM), indole‐based ‐QM analog. These transient species are often utilized for direct enantioselective synthesis of complex (hetero)polycyclic or fused‐ring molecular scaffolds such as tetrahydroquinoline indoline, among others, which abundant many natural products, bioactive compounds, pharmaceuticals.

Язык: Английский

Organocatalytic Formal (3 + 2) Cycloaddition toward Chiral Pyrrolo[1,2-a]indoles via Dynamic Kinetic Resolution of Allene Intermediates DOI
Jian‐Fei Bai, Lulu Zhao,

Fang Wang

и другие.

Organic Letters, Год журнала: 2020, Номер 22(14), С. 5439 - 5445

Опубликована: Июнь 29, 2020

We report the chiral phosphoric acid catalyzed formal (3 + 2) cycloaddition of 3-substituted 1H-indoles and propargylic alcohols containing a functional directing group (p-NHAc or p-OH). This work represents straightforward method to synthesize pyrrolo[1,2-a]indole bearing tetrasubstituted carbon stereocenter. The reaction proceeds smoothly with wide array substrate tolerance deliver various pyrrolo[1,2-a]indoles in up 93% yield 98% ee. utility this is highlighted by diverse transformations products into indole derivatives.

Язык: Английский

Процитировано

45
Organocatalytic stereoselective 1,6-addition of thiolacetic acids to alkynyl indole imine methides: access to axially chiral sulfur-containing tetrasubstituted allenes DOI
Ziyang Wang, Xiao Lin, Xuling Chen

и другие.

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(13), С. 3469 - 3474

Опубликована: Янв. 1, 2021

A chiral phosphoric acid-catalyzed enantioselective 1,6-conjugate addition of thiolacetic acid to alkynyl indole imine methide in situ formed from α-(3-indolyl) propargylic alcohol has been established.

Язык: Английский

Процитировано

39
Catalyst-Controlled Divergent Reactions of 2,3-Disubstituted Indoles with Propargylic Alcohols: Synthesis of 3H-Benzo[b]azepines and Axially Chiral Tetrasubstituted Allenes DOI

Chenxiao Qian,

Tingting Huang, Jianwei Sun

и другие.

Organic Letters, Год журнала: 2022, Номер 24(35), С. 6472 - 6476

Опубликована: Авг. 30, 2022

Catalyst-controlled divergent reactions of 2,3-disubstituted indoles with propargylic alcohols were developed for the first time. In presence TsOH or B(C6F5)3 as catalyst, reacted smoothly 3-alkynyl-3-hydroxyisoindolinones to afford 3H-benzo[b]azepines by selective C2(sp2)-C3(sp2) ring expansion indoles. contrast, decreasing catalyst strength (e.g., chiral phosphoric acid) interrupted cascade reactions, affording axially tetrasubstituted allenes bearing an adjacent quaternary carbon stereocenter. Control experiments provided insights into reaction mechanism.

Язык: Английский

Процитировано

27
Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality DOI
Yan Xia,

Meiwen Liu,

Chenxiao Qian

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 10(1), С. 30 - 34

Опубликована: Ноя. 14, 2022

Organocatalytic enantioselective construction of chiral spiro N , -acetal carbon stereocenters and axially 3-arylindoles has been achieved in one pot.

Язык: Английский

Процитировано

27
Aza‐Ortho‐Quinone Methides as Reactive Intermediates: Generation and Utility in Contemporary Asymmetric Synthesis DOI
Hsuan‐Hung Liao, Shinje Miñoza, Shao‐Chi Lee

и другие.

Chemistry - A European Journal, Год журнала: 2022, Номер 28(46)

Опубликована: Июнь 2, 2022

Abstract The aza‐ ortho ‐quinone methide (aza‐ o ‐QM) chemistry has overwhelmingly progressed in the past few decades. This review aims to integrate various transition metal‐catalyzed and organocatalytic strategies taming aza ‐o‐ QM intermediates, including ‐vinylidene quinone ‐VQM), ‐alkynyl ‐AQM), para p ‐QM), indole‐based ‐QM analog. These transient species are often utilized for direct enantioselective synthesis of complex (hetero)polycyclic or fused‐ring molecular scaffolds such as tetrahydroquinoline indoline, among others, which abundant many natural products, bioactive compounds, pharmaceuticals.

Язык: Английский

Процитировано

24