Enantioselecitve Allylation/Retro-Claisen Cascade DOI
Mark Lautens, Alexa Torelli

Synfacts, Journal Year: 2022, Volume and Issue: 19(01), P. 0056 - 0056

Published: Dec. 16, 2022

Key words iridium catalysis - allylation Claisen reaction vinylethylene carbonate

Language: Английский

Asymmetric Retro-Claisen Reaction Catalyzed by Chiral Aza-Bisoxazoline–Zn(II) Complex: Enantioselective Synthesis of α-Arylated Ketones DOI
Jiahui Liu,

Xuejiao Lv,

Yankai Liu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1706 - 1710

Published: March 7, 2023

An asymmetric retro-Claisen reaction of α-monosubstituted β-diketones and quinones (or quinone imine) has been developed under the catalysis a chiral aza-bisoxazoline–Zn(II) complex. The proceeds via sequence conjugate addition, arylation, hemiketal anion-initiated C–C bond cleavage, enantioselective protonation enolate to provide various functionalized α-arylated ketones bearing tertiary stereogenic center with high enantioselectivities. Notably, biologically important benzofuran γ-butyrolactone derivatives could be synthesized by application protocol.

Language: Английский

Citations

6
Enantioselective synthesis of 2-amino-4H-chromene derivatives with antifungal activities on phytopathogenic fungi DOI
Man Zhang,

Yifan Ru,

Shilin Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3692 - 3699

Published: Jan. 1, 2024

An Ir-catalyzed enantioselective cascade allylation/cyclization reaction of 2-(1-hydroxyallyl)phenols was developed, affording antifungal 2-amino-4 H -chromene derivatives with good to excellent enantioselectivities.

Language: Английский

Citations

1
Visible-Light-Photocatalyzed Self-Cyclopropanation Reactions of Dibenzoylmethanes for the Synthesis of Cyclopropanes DOI
Ranadheer Reddy Indurmuddam, Pei-Chi Huang, Bor‐Cherng Hong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5752 - 5757

Published: July 1, 2024

A new self-cyclopropanation of 1,3-diphenylpropane-1,3-dione, leading to tetrasubstituted cyclopropane containing three contiguous stereogenic centers with high stereoselectivity, has been achieved through violet-light-emitting diode-irradiated photocatalysis, featuring both cycloaddition and a distinctive rearrangement. Diverging from conventional cyclopropanation pathways, this reaction yields unprecedented rearrangement cascade reactions.

Language: Английский

Citations

1
Acyl transfer-enabled catalytic asymmetric Michael addition of α-hydroxy-1-indanones to nitroolefins DOI Open Access
Zhihua Xu, Na Li,

Zhe‐Ran Chang

et al.

Chemical Synthesis, Journal Year: 2023, Volume and Issue: 3(2), P. 17 - 17

Published: Jan. 1, 2023

We report herein an enantioselective acyl transfer protocol via electrophile activation. The reaction cascade sequence encompasses dinuclear zinc-catalyzed asymmetric Michael addition, intramolecular cyclization, and retro-Claisen reaction, which leads to a step- atom-economic approach variety of protected cyclic tertiary α-hydroxyketones in good yields with excellent enantioselectivities (24 examples, 56%-82% yield, 1.5-13 dr 79%-96% ee). Besides, the large-scale synthesis further transformation products demonstrate effectiveness this method for organic synthesis.

Language: Английский

Citations

2
Ir/Brønsted acid dual-catalyzed asymmetric synthesis of bisbenzannulated spiroketals and spiroaminals from isochroman ketals DOI
Yang Chen, Hui Yan, Hanliang Zheng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5831 - 5840

Published: Jan. 1, 2024

An Ir/Brønsted acid dual-catalyzed asymmetric cascade reaction of 2-(1-hydroxyallyl)phenols with isochroman ketals was developed, affording antifungal spiroketals high enantioselectivities.

Language: Английский

Citations

0
Iridium-Catalyzed Asymmetric Cascade Allylation/[1,4]-Phospha-Brook Rearrangement Reaction DOI

Zhiyuan Yi,

Hui Xu, Xin Chang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 14058 - 14068

Published: Sept. 10, 2024

Language: Английский

Citations

0
Ir‐Catalyzed Enantioselective Synthesis of gem‐Diborylalkenes Enabled by 1,2‐Boron Shift DOI

Jianfei Ge,

Xi‐Zhang Zou,

Xinru Liu

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(32)

Published: June 15, 2023

Abstract Asymmetric cross‐couplings based on 1,2‐carbon migration from B‐ate complexes have been developed efficiently to access valuable organoboronates. However, enantioselective reactions triggered by 1,2‐boron shift remained be unaddressed synthetic challenge. Here, Ir‐catalyzed asymmetric allylic alkylation enabled was developed. In this reaction, we disclosed that excellent enantioselectivities were achieved through an interesting dynamic kinetic resolution (DKR) process of carbonates at the elevated temperature. Notably, highly (bis‐boryl)alkenes array diversifications versatile molecules. Extensive experimental and computational studies conducted elucidate reaction mechanism DKR clarify origin enantioselectivities.

Language: Английский

Citations

1
Iridium-catalyzed asymmetric cascade dearomative allylation/acyl transfer rearrangement: access to chiral N-substituted 2-pyridones DOI
Weiyi Wang,

Zhiyuan Yi,

Zuo-Fei Wang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(38), P. 5086 - 5089

Published: Jan. 1, 2024

Iridium-catalyzed dearomative allylation/acyl transfer rearrangement has been developed using easily available 2-pyridinyl benzoates and vinyl ethylene carbonate. This protocol enabled the expedient synthesis of a variety chiral

Language: Английский

Citations

0
Regioselective Formal β‐Allylation of Carbonyl Compounds Enabled by Cooperative Nickel and Photoredox Catalysis DOI
Kun Liu, Zhe Wang,

Augustinus N. Künzel

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(37)

Published: May 4, 2023

Abstract The Tsuji–Trost reaction between carbonyl compounds and allylic precursors has been widely used in the synthesis of natural products pharmaceutical compounds. As α‐C−H bond is far more acidic than β‐C−H bond, undergo highly regioselective allylation at α‐position their β‐allylation therefore challenging. This innate α‐reactivity conversely hampers diversity, especially if corresponding product targeted. Herein, we present a formal intermolecular β‐C−C formation broad range aldehydes ketones with different allyl electrophiles through cooperative nickel photoredox catalysis. β‐Selectivity achieved via initial transformation to silyl enol ethers. overall features mild conditions, excellent regioselectivity, wide functional group tolerance high efficiency. introduced facile proceeding catalysis allows preparation valuable building blocks that are difficult access from using existing methodology.

Language: Английский

Citations

0
Enantioselecitve Allylation/Retro-Claisen Cascade DOI
Mark Lautens, Alexa Torelli

Synfacts, Journal Year: 2022, Volume and Issue: 19(01), P. 0056 - 0056

Published: Dec. 16, 2022

Key words iridium catalysis - allylation Claisen reaction vinylethylene carbonate

Language: Английский

Citations

0