Brønsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo‐ and Enantioselective Synthesis of Spirolactams DOI
Pengfei Chen, Bo Zhou, Peng Wu

et al.

Angewandte Chemie, Journal Year: 2021, Volume and Issue: 133(52), P. 27370 - 27376

Published: Oct. 21, 2021

Abstract Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom‐economic synthesis of range valuable spirolactams from readily available ynamides in generally good to excellent yields with diastereoselectivities broad substrate scope. Importantly, an unexpected dearomatization nonactivated arenes heteroaromatic compounds involved this tandem sequence. Moreover, asymmetric version cyclization was also achieved by efficient kinetic resolution chiral phosphoric catalysis. In addition, [3,3]‐rearrangement shown be kinetically preferred over related [1,3]‐rearrangement theoretical calculations.

Language: Английский

Controllable cyclization of alkynyl thioethersviaBrønsted acid-catalyzed dearomatization DOI

Xin-Yang Fan,

Xin Liu,

Yin-Zhu Kong

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(11), P. 2766 - 2772

Published: Jan. 1, 2023

An efficient and controllable cyclization of alkynyl thioethers via Brønsted acid-catalyzed dearomatization is described, enabling practical atom-economical synthesis valuable spirohexenones phenanthrols in generally excellent yields.

Language: Английский

Citations

5
Iron-catalyzed divergent approach to naphthyridinones and quinolinones: leveraging Povarov and carbonyl-alkyne metathesis reactions of electron deficient alkynes DOI
Jiaming Chen, Junhua Li,

Licheng Xie

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(21), P. 5505 - 5511

Published: Jan. 1, 2023

We have successfully developed a novel synthetic route for the synthesis of naphthyridinones.

Language: Английский

Citations

5
Copper‐Catalyzed Asymmetric Diyne Cyclization via [1,2]‐Stevens‐Type Rearrangement for the Synthesis of Chiral Chromeno[3,4‐c]pyrroles DOI

Feng‐Lin Hong,

Chong‐Yang Shi,

Pan Hong

et al.

Angewandte Chemie, Journal Year: 2021, Volume and Issue: 134(7)

Published: Dec. 14, 2021

Abstract Here, we report a copper‐catalyzed asymmetric cascade cyclization/[1,2]‐Stevens‐type rearrangement via non‐diazo approach, leading to the practical and atom‐economic assembly of various valuable chiral chromeno[3,4‐ c ]pyrroles bearing quaternary carbon stereocenter in generally moderate good yields with wide substrate scope excellent enantioselectivities (up 99 % ee). Importantly, this protocol not only represents first example catalytic [1,2]‐Stevens‐type based on alkynes but also constitutes formal carbene insertion into Si−O bond .

Language: Английский

Citations

12
Copper-Catalyzed Si–H Bond Insertion Reaction of N-Propargyl Ynamides with Hydrosilanes DOI

En‐He Huang,

Yingqi Zhang,

Da-Qiu Cui

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 24(1), P. 196 - 201

Published: Dec. 21, 2021

Transition-metal-catalyzed Si-H bond insertion reactions are generally limited to stabilized diazo compounds. An efficient copper-catalyzed reaction of N-propargyl ynamides with hydrosilanes is described, allowing practical and atom-economic construction valuable organosilanes in moderate excellent yields under mild conditions. Notably, this constitutes a new method involving vinyl cations as key intermediates.

Language: Английский

Citations

12
Brønsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo‐ and Enantioselective Synthesis of Spirolactams DOI
Pengfei Chen, Bo Zhou, Peng Wu

et al.

Angewandte Chemie, Journal Year: 2021, Volume and Issue: 133(52), P. 27370 - 27376

Published: Oct. 21, 2021

Abstract Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom‐economic synthesis of range valuable spirolactams from readily available ynamides in generally good to excellent yields with diastereoselectivities broad substrate scope. Importantly, an unexpected dearomatization nonactivated arenes heteroaromatic compounds involved this tandem sequence. Moreover, asymmetric version cyclization was also achieved by efficient kinetic resolution chiral phosphoric catalysis. In addition, [3,3]‐rearrangement shown be kinetically preferred over related [1,3]‐rearrangement theoretical calculations.

Language: Английский

Citations

12