Enantioselective (3+2)-Annulation of β-Keto Esters with Azoalkenes towards Bicyclic Dihydropyrroles via Cooperative Palladium and Brønsted Acid Catalysis DOI
Christoph Schneider,

Till Friedmann,

Daniel A. Mireles-Chávez

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(09), P. 997 - 1000

Published: Nov. 13, 2023

Abstract A cooperative catalytic process through palladium and Brønsted acid activation is developed for the conjugate addition of cyclic β-keto esters to azoalkenes directly followed by hemiaminal formation upon cyclization. This transformation enabled utilizing chiral Pd-aqua complexes as combined acid–base catalysts. Thus, bicyclic highly functionalized dihydropyrroles with two contiguous quaternary stereogenic centers are formed in excellent yields single diastereomers exceptional enantioselectivity.

Language: Английский

Diversity‐Oriented Catalytic Asymmetric Dearomatization of Indoles with o‐Quinone Diimides DOI Creative Commons

Hao‐Jie Gao,

Yu‐Hang Miao,

Wen‐Na Sun

et al.

Advanced Science, Journal Year: 2023, Volume and Issue: 10(35)

Published: Oct. 23, 2023

Abstract Herein, the first diversity‐oriented catalytic asymmetric dearomatization of indoles with o ‐quinone diimides ( ‐QDIs) is reported. The (CADA) one research focuses in terms structural and biological importance dearomatized indole derivatives. Although great achievements have been made target‐oriented CADA reactions, reactions are regarded as more challenging remain elusive due to lack synthons featuring multiple reaction sites difficulty precise control chemo‐, regio‐, enantio‐selectivity. In this work, ‐QDIs employed a versatile building block, enabling chemo‐divergent dearomative arylation [4 + 2] cycloaddition indoles. Under catalysis chiral phosphoric acid mild conditions, various indolenines, furoindolines/pyrroloindolines, six‐membered‐ring fused indolines collectively prepared good yields excellent enantioselectivities. This synthesis protocol enriches chemistry offers new opportunities for reactions.

Language: Английский

Citations

13
Catalytic Asymmetric Rearrangement of Azoalkene-Derived Sulfonium Ylides via Remote Chirality Control DOI
Kaixuan Wang,

Zhiqian Yu,

Zheng Tan

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

The [2,3]-sigmatropic rearrangement has been widely utilized to construct C-S bonds. Herein, we report an enantioselective, intermolecular, and noncarbenoid of sulfonium ylides using azoalkenes. This process features a broad substrate scope, high efficiency, excellent enantioselectivity, achieving yields up 99% enantiomeric excess (ee) 96%. Furthermore, the protocol demonstrated good scalability.

Language: Английский

Citations

0
Annulated and spiro-molecular systems from cycloheptane-based β-ketoesters: Synthesis, reactivity, and biological applications DOI
Sherif M. H. Sanad, Ahmed E. M. Mekky,

Rahma M.B. Hussein

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: unknown, P. 141274 - 141274

Published: Dec. 1, 2024

Language: Английский

Citations

3
Catalyst-free racemic and H2O/CPA-catalyzed asymmetric regio-reversed domino processes of triketone enones with azlactones DOI

Yun-Dong Fu,

Xiang Gao, Shi‐Kun Jia

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(14), P. 5692 - 5697

Published: Jan. 1, 2023

The first regio-reversed domino processes of triketone enones with azlactones are established leading to the formation a variety bicyclic furofurans bearing vicinal quaternary carbons in good excellent yields.

Language: Английский

Citations

8
Diastereodivergent and Regioselective Synthesis of Tetrahydrofuro[2,3-b]furans with Four Consecutive Stereocenters DOI
Jing Zhang,

Wen‐Na Sun,

Zhiwei Jiang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4134 - 4144

Published: Feb. 23, 2024

Base-catalyzed diastereodivergent and regioselective domino processes of triketone enones with arylacetaldehydes for the synthesis tetrahydrofuro[2,3-

Language: Английский

Citations

1
Interrupted Plancher Rearrangement Initiated by Dearomative Epoxide–Indole Cyclization: Formal Umpolung Reactivity of Indoles DOI

Raju Chouhan,

Sajal Kumar Das

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 12, 2024

We herein report the serendipitous discovery of interrupted Plancher rearrangement initiated by an HFIP-promoted dearomative epoxide-indole cyclization, unlocking a new blueprint to formal C3 umpolung reactivity indoles. This rapid complexity generating cascade process paves way toward class fused-bridged indolines in high yields and under full regio- diastereocontrol. The reaction is amenable wide range substituents starting materials.

Language: Английский

Citations

1
Five-membered ring systems: Pyrroles and benzo analogs DOI
Chuan Shan, Justin M. Lopchuk

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173

Published: Jan. 1, 2024

Language: Английский

Citations

0
Enantioselective (3+2)-Annulation of β-Keto Esters with Azoalkenes towards Bicyclic Dihydropyrroles via Cooperative Palladium and Brønsted Acid Catalysis DOI
Christoph Schneider,

Till Friedmann,

Daniel A. Mireles-Chávez

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(09), P. 997 - 1000

Published: Nov. 13, 2023

Abstract A cooperative catalytic process through palladium and Brønsted acid activation is developed for the conjugate addition of cyclic β-keto esters to azoalkenes directly followed by hemiaminal formation upon cyclization. This transformation enabled utilizing chiral Pd-aqua complexes as combined acid–base catalysts. Thus, bicyclic highly functionalized dihydropyrroles with two contiguous quaternary stereogenic centers are formed in excellent yields single diastereomers exceptional enantioselectivity.

Language: Английский

Citations

0