Gold-catalyzed domino reactions of alkynol and <i>p</i>-quinone methides: divergent synthesis of fused- and spiro-ketals

Mao, Wenxiu; Lin, Shiquan; Zhang, Liang; Lu, Haifeng; Jia, Jiong; Xu, Zhenghu

doi:10.1039/d0qo00022a

Cited by 24 publications

(6 citation statements)

References 72 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In this context, Jia and Xu et al also demonstrated a gold-catalyzed cyclization of pquinone methides with in situ generated cyclic enol ethers toward the construction of spiro and fused ketals. 9 Over time, donor−acceptor cyclopropane carbaldehydes have emerged as versatile synthons for the diverse hetero/carbocyclic synthesis. 10,11 In this regard, our group has significantly explored the strain-driven reactivity of aryl-substituted cyclopropane carbaldehydes (ACC) toward heterocyclic synthesis via Lewisacid or metal-free activation of the cyclopropane ring.…”

Section: ■ Introductionmentioning

confidence: 99%

Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters

et al. 2022

View full text Add to dashboard Cite

Herein, we report a straightforward one-pot synthesis of tetrahydrofurobenzopyran and tetrahydrofurobenzofuran systems via an in situ ring-expansion of the cyclopropane carbaldehydes followed by a [2 + n] cycloaddition with the quinone derivatives. The transformation not only unveils a new reaction mode of cyclopropane carbaldehydes with quinone methides/esters, but also promotes a step-efficient diastereoselective route to the sophisticatedly fused oxygen tricycles that can be further dehydrogenated to access the valued dihydro-2H-furo[2,3-b]chromene frameworks.

show abstract

Section: ■ Introductionmentioning

confidence: 99%

Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Later, Jia and Xu developed similar gold-catalyzed protocol to access spirocyclic chromane derivatives from 16 and 1,3-alkynyl alcohols and/or o-alkynyl benzyl alcohols. [57] A chiral thiourea (133) catalyzed highly enantioselective reaction between 16 and isaitin-derived enediones (131), to synthesize enantiomerically pure spirocyclic chromane derivatives (132), has been developed by Enders and co-workers (Scheme 32). [58] Many chiral spirocyclic chromane desrivatives (132) have been prepared by this method in excellent yields and enantio-/diastereo-selectivity (dr up to > 20 : 1 ee > 99 %).…”

Section: Synthesis Of Spirocyclic Chromane and Tetrahydropyran Derivativesmentioning

confidence: 99%

Construction of Oxygen‐ and Nitrogen‐based Heterocycles from p‐Quinone Methides

Singh

Pandey

Pankhade

et al. 2021

The Chemical Record

View full text Add to dashboard Cite

In the last few years, there has been an explosive growth in the area of para-quinone methide (p-QM) chemistry. This boom is actually due to the unique reactivity pattern of p-QMs, and also their remarkable synthetic applications. In fact, p-QMs serve as synthons for unsymmetrical diaryl-and triarylmethanes, and also for the construction of diverse range of carbocycles and heterocycles. In the last few years, a wide range of structurally complex heterocyclic frameworks could be accessed through the synthetic transformations of structurally modified stable p-QMs. Therefore, the main focus of this review article is to cover the recent advancements in the transition-metal, Lewis acid and base-catalyzed/mediated synthetic transformations of the stable p-quinone methides (p-QMs) to oxygen-and nitrogen-containing heterocycles.

show abstract

“…Recently, Au/Lewis acid bimetallic catalysis has been exploited to be a strategy to construct aminals and ketals via 5-exo-dig cyclization of alkynyl amides or alcohols and relay cycloaddition reactions with electrophiles 42 – 49 . Moreover, Feng’s group developed the first highly efficient asymmetric bimetallic Au(I)/chiral Ni(II) catalytic cascade reaction of α, β -unsaturated γ -keto esters with alkynyl amides and alcohols for the synthesis of spiroketals and spiroaminals in 2016 50 .…”

Section: Introductionmentioning

confidence: 99%

Biomimetic approach to the catalytic enantioselective synthesis of tetracyclic isochroman

et al. 2021

View full text Add to dashboard Cite

Polyketide oligomers containing the structure of tetracyclic isochroman comprise a large class of natural products with diverse activity. However, a general and stereoselective method towards the rapid construction of this structure remains challenging due to the inherent instability and complex stereochemistry of polyketide. By mimicking the biosynthetic pathway of this structurally diverse set of natural products, we herein develop an asymmetric hetero-Diels–Alder reaction of in-situ generated isochromene and ortho-quinonemethide. A broad range of tetracyclic isochroman frameworks are prepared in good yields and excellent stereoinduction (up to 95% ee) from readily available α-propargyl benzyl alcohols and 2-(hydroxylmethyl) phenols under mild conditions. This direct enantioselective cascade reaction is achieved by a Au(I)/chiral Sc(III) bimetallic catalytic system. Experimental studies indicate that the key hetero-Diels-Alder reaction involves a stepwise pathway, and the steric hindrance between in-situ generated isochromene and t-Bu group of Sc(III)/N,N’-dioxide complex is responsible for the enantioselectivity in the hetero-Diels–Alder reaction step.

show abstract

Gold-catalyzed domino reactions of alkynol and p-quinone methides: divergent synthesis of fused- and spiro-ketals

Abstract: A gold-catalyzed domino reaction of alkynyl alcohols and p-quinone methides to obtain divergent fused- and spiro-ketals has been developed.

Cited by 24 publications

References 72 publications

Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters

Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters

Construction of Oxygen‐ and Nitrogen‐based Heterocycles from p‐Quinone Methides

Biomimetic approach to the catalytic enantioselective synthesis of tetracyclic isochroman

Contact Info

Product

Resources

About