Heterobimetallic Zinc/Strontium Catalysis: Z/E-Selective Asymmetric Conjugate Addition of 3-Acetoxy-2-oxindoles to Alkynones DOI

Junyu Zhou,

Peng Chen,

Guojuan Liang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12307 - 12317

Опубликована: Авг. 27, 2024

A chiral Zn–Sr heterobimetallic catalyst system generated in situ has been developed for the first highly Z/E-selective asymmetric conjugate addition of 3-acetoxy-2-oxindoles to alkynones. Both terminal alkynones and nonterminal could be applied catalytic system. The corresponding 3-alkenyl-3-acyloxy-2-oxindoles were obtained moderate excellent yields (55–99%) with high E:Z ratios (8:1–30:1) enantioselectivities (86–99% ee).

Язык: Английский

Access to Tetrahydrothiopyrano[2,3‐b]Indole Derivatives via Zinc‐Catalyzed Asymmetric [3+3] Annulation of Indoline‐2‐Thiones with Yne–Enones DOI

Dandan Cui,

Jian‐Wen Shi, Tong Wang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1770 - 1775

Опубликована: Март 1, 2024

Abstract We report herein an enantioselective [3+3] annulation of indoline‐2‐thiones with yne–enones by chiral dinuclear zinc catalysts via a Brønsted base and Lewis acid cooperative activation model. This transformation proceeded through sequential conjugate addition, allenyl ketone formation intramolecular sulfa‐Michael 6‐ endo ‐trig cyclization. A range enantioenriched tetrahydrothiopyrano[2,3‐ b ]indole derivatives bearing exocyclic double bond were obtained in moderate yields excellent stereoselectivities (up to 20 : 1 dr, 20:1 Z/E ratio 95% ee). Late‐stage functionalization, large‐scale experiment further derivatizations also explored.

Язык: Английский

Процитировано

7

Asymmetric synthesis of bicyclic pyran scaffolds bearing two oxa-quaternary stereocenters via zinc-catalyzed [5 + 1] annulations DOI
Cui Zhang, Tao Jiang, Yuan‐Zhao Hua

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(18), С. 4516 - 4521

Опубликована: Янв. 1, 2023

Zinc-catalyzed [5 + 1] annulation of α-hydroxyl aryl ketones with cyclohexadienone-tethered enones has been developed, giving access to enantioenriched bicyclic pyran scaffolds bearing two oxa-quaternary stereocenters.

Язык: Английский

Процитировано

7

Manipulating Activity and Chemoselectivity of a Benzaldehyde Lyase for Efficient Synthesis of α-Hydroxymethyl Ketones and One-Pot Enantio-Complementary Conversion to 1,2-Diols DOI
Yifan Zhang, Yu Li, Yangyang Chen

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(13), С. 9687 - 9700

Опубликована: Июнь 13, 2024

The α-hydroxymethyl ketone motif has been widely found in many pharmaceutically important molecules and used as a key intermediate the synthesis of various fine chemicals natural products. Hydroxymethylation aldehydes with formaldehyde catalyzed by thiamine diphosphate (ThDP)-dependent enzymes is considered highly valuable approach terms atom economics sustainability, while low activity chemoselectivity restricted its widespread application. In this study, benzaldehyde lyase (BAL) high catalytic efficiency was acquired enzyme screening engineering, which hydroxymethylation furfural at concentration 700 mM. Crystal structural analysis molecular dynamics studies revealed that BAL were improved reshaping conformation substrate entrance tunnel. Furthermore, one-pot concurrent enzymatic process involving BAL-catalyzed subsequent asymmetric reduction carbonyl reductase developed, offering efficient way to produce chiral 1,2-diols from simple aldehydes, ee values (97–99%) good yields (52–97%). significantly demonstrated potential engineered industrial production ketones, could readily enable other high-value-added formaldehyde.

Язык: Английский

Процитировано

2

Enantioselective access to spiro[2,3-dihydrofuran-2,2′-inden-1-ones]viazinc catalyzed [3 + 2] annulation of α-hydroxy-1-indanones with yne–enones DOI
Jiaojiao Han, Tao Jiang, Cui Zhang

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(16), С. 4061 - 4067

Опубликована: Янв. 1, 2023

An enantioselective construction of spiro[1-indanone-dihydrofurans] has been accomplished through zinc-catalyzed [3 + 2] annulation via a Brønsted base and Lewis acid cooperative activation model.

Язык: Английский

Процитировано

5

Dinuclear Zinc Catalyzed [3+2] Annulation of Benzylideneindolinones Access to CF3‐Containing 2,3‐Pyrrolidinyl Dispirooxindoles DOI Open Access

Ying‐Hui Zhai,

Ya‐Jun Guo,

Si‐Si Du

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(18), С. 3088 - 3093

Опубликована: Авг. 9, 2023

Abstract This report has realized the catalytic asymmetric [3+2] annulation of benzylideneindolinones with CF 3 ‐containing isatin‐derived azomethine ylides for first time, in which organocatalysis failed. In presence dinuclear zinc catalysts, a series functionalized 2,3‐pyrrolidinyl dispirooxindoles have been synthesized good yields excellent stereoselectivity under mild reaction conditions. protocol can be run on gram scale and possible mechanism is proposed.

Язык: Английский

Процитировано

4

Dinuclear Zinc‐Catalyzed Asymmetric Desymmetrization of Cyclopentendiones: Access to Functional Cyclopentanediones Bearing an All‐carbon Quaternary Stereocenter DOI

Si‐Si Du,

Ying‐Hui Zhai,

Cui Zhang

и другие.

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(18)

Опубликована: Авг. 1, 2023

The success in the identification of two enantioisomeric surfaces electrophiles by dinuclear zinc catalysts is disclosed. This protocol realizes a zinc-cocatalyzed desymmetrization cyclopentendiones using α-hydroxy aryl ketones as nucleophiles through Michael addition reaction. Under mild conditions, series functional cyclopentanediones bearing multiple stereogenic centers including an all-carbon quaternary stereocenter, were obtained moderate to good yields with excellent stereoselectivities.

Язык: Английский

Процитировано

1

Dinuclear zinc catalysis of a kinetic resolution strategy for distinguishing one pair of diastereoisomers from multiple stereoisomers DOI

Ying-Hui Zhai,

Jia-Qi Wen,

Mengmeng Liu

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(18), С. 5172 - 5178

Опубликована: Янв. 1, 2024

A new kinetic resolution strategy of distinguishing four stereoisomers is realized by dinuclear zinc catalysts.

Язык: Английский

Процитировано

0

Heterobimetallic Zinc/Strontium Catalysis: Z/E-Selective Asymmetric Conjugate Addition of 3-Acetoxy-2-oxindoles to Alkynones DOI

Junyu Zhou,

Peng Chen,

Guojuan Liang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12307 - 12317

Опубликована: Авг. 27, 2024

A chiral Zn–Sr heterobimetallic catalyst system generated in situ has been developed for the first highly Z/E-selective asymmetric conjugate addition of 3-acetoxy-2-oxindoles to alkynones. Both terminal alkynones and nonterminal could be applied catalytic system. The corresponding 3-alkenyl-3-acyloxy-2-oxindoles were obtained moderate excellent yields (55–99%) with high E:Z ratios (8:1–30:1) enantioselectivities (86–99% ee).

Язык: Английский

Процитировано

0