Lanthanide amide-catalyzed one-pot functionalization of isatins: synthesis of spiro[cyclopropan-1,3′-oxindoles] and 2-oxoindolin-3-yl phosphates

2017 ◽  
Vol 15 (18) ◽  
pp. 3968-3974 ◽  
Author(s):  
Cheng Peng ◽  
Jiaojiao Zhai ◽  
Mingqiang Xue ◽  
Fan Xu
Keyword(s):  
One Pot ◽  
Lanthanide Amide ◽  
High Stereoselectivity

A lanthanide-catalyzed one-pot reaction using readily accessible substrates was developed affording spiro[cyclopropan-1,3′-oxindoles] in good yields and with high stereoselectivity.

Diastereoselective synthesis of α-dicarbonyl cyclopropanes via a lanthanide amide-catalysed reaction

2019 ◽  
Vol 17 (27) ◽  
pp. 6620-6628
Author(s):  
Wenxi Sun ◽  
Cheng Peng ◽  
Zhigang Yao ◽  
Fan Xu
Keyword(s):  
Diastereoselective Synthesis ◽  
One Pot ◽  
Catalysed Reaction ◽  
Lanthanide Amide ◽  
High Stereoselectivity

A lanthanide amide-catalyzed one-pot reaction was developed affording α-dicarbonyl cyclopropanes in good yields and with high stereoselectivity.

An Efficient One-Pot Method for a Highly Stereoselective Base-Catalysed Synthesis of Novel Trans-Spirocyclopropane-Indanedione Derivatives

2017 ◽  
Vol 41 (10) ◽  
pp. 611-613 ◽  
Author(s):  
Azadeh Havasian ◽  
Mohammad H. Mosslemin ◽  
Mohammad R. Nateghi ◽  
Forough Kalantari-Fotooh
Keyword(s):  
High Purity ◽  
Reaction Times ◽  
Efficient Synthesis ◽  
One Pot ◽  
Work Up ◽  
High Stereoselectivity

A one-pot, efficient, synthesis of six novel trans-spirocyclopropane-indanedione derivatives with high stereoselectivity has been achieved via the reaction of acetopyridinium chloride with 1,3-indandione and an araldehyde in the presence of triethylamine in acetonitrile under reflux conditions. The attractive features of the method are excellent yields and high purity, short reaction times, and easy work-up.

ChemInform Abstract: High Stereoselectivity in One-Pot Intramolecular Cycloadditions of Olefinic Silyl Nitronates.

ChemInform ◽  
2010 ◽  
Vol 31 (2) ◽  
pp. no-no
Author(s):  
Qian Cheng ◽  
Takayuki Oritani ◽  
Tohru Horiguchi ◽  
Qingwen Shi
Keyword(s):  
One Pot ◽  
Silyl Nitronates ◽  
Intramolecular Cycloadditions ◽  
High Stereoselectivity

Preparation of Bicyclic Ketal Skeletons with Aldehyde and α-Ketone Acid through Cascade Friedel–Crafts Reaction and Stereoselective Acetalization in One Pot

Synlett ◽  
2019 ◽  
Vol 30 (18) ◽  
pp. 2091-2095
Author(s):  
Ling Li ◽  
Ying-wei Wang ◽  
Shi-qi Zhang ◽  
Xiong-fei Deng ◽  
Guang-xun Li ◽  
...  
Keyword(s):  
Natural Products ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
One Pot ◽  
Brönsted Acid ◽  
High Stereoselectivity ◽  
Moderate Yield ◽  
Important Structure

Bicyclic ketal skeletons are important structure fragments that are frequently contained in natural products. A novel tandem Friedel–Crafts reaction and subsequent stereoselective acetalization were developed with readily available aldehyde and ketone acid. The reaction proceeded smoothly in the presence of catalytic Brønsted acid and afforded the corresponding product with moderate yield and high stereoselectivity.

Proline triflate catalysed Diels–Alder reaction in the synthesis of tetrahydroquinoline derivatives

2009 ◽  
Vol 2009 (8) ◽  
pp. 499-504 ◽  
Author(s):  
Jianjun Li ◽  
Jia Li ◽  
Weike Su
Keyword(s):  
Aromatic Amines ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
The One ◽  
High Stereoselectivity

Proline triflate was found to catalyse efficiently the one-pot synthesis of 2H-pyranotetrahydroquinolines from aryl imines, and 3,4-dihydro-2 H-pyran with high stereoselectivity. The aryl imines were formed in situ from aromatic amines and arylaldehydes.

scholarly journals Multi-Catalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols

2021 ◽  
Author(s):  
Alessandra Casnati ◽  
Dawid Lichosyt ◽  
Bruno Lainer ◽  
Lukas Veth ◽  
Pawel Dydio
Keyword(s):  
Stereoselective Synthesis ◽  
Value Added ◽  
Cross Reactivity ◽  
Transition Metal Catalysts ◽  
Allylic Alcohols ◽  
One Pot ◽  
Benzylic Alcohols ◽  
Material Efficiency ◽  
The One ◽  
High Stereoselectivity

One-pot multi-step procedures bear the potential to rapidly build up molecular complexity while avoiding the wasteful and costly isolations and purifications of consecutive intermediates. Here we report multi-catalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Because each transformation of the sequence is executed by an independent catalyst, without any catalytic cross-reactivity, allylic alcohols bearing a prochiral double bond can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er and >20:1 dr). Overall, with the aid of up to four catalysts operating in a single vessel, the protocols directly convert simple starting materials into a range of value-added products with high stereocontrol and excellent material efficiency, demonstrating both the efficacy and the advantages of the one-pot synthesis employing multiple transition-metal catalysts.

One-Pot Catalyst-Free Domino Condensation/Intramolecular 1,3-Dipolar Cycloaddition: Highly Stereoselective Access to Phosphadihydrocoumarin-Fused N,N-Bicyclic Pyrazolidin-3-ones

Synthesis ◽  
2017 ◽  
Vol 50 (01) ◽  
pp. 139-145 ◽  
Author(s):  
Mingshu Wu ◽  
Jie Jiang ◽  
Zhongxiang Zhu ◽  
Qinghe Wang ◽  
Dulin Kong
Keyword(s):  
Low Cost ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Nitrogen And Phosphorus ◽  
One Pot ◽  
Intramolecular Cycloaddition ◽  
Catalyst Free ◽  
Synthetic Strategy ◽  
The One ◽  
High Stereoselectivity

A concise, atom-economic, and highly regio/stereoselective synthetic strategy was developed for the construction of phosphorus- and nitrogen-fused polycyclic skeleton derivatives. The one-pot, two-step, catalyst-free domino condensation/intramolecular cycloaddition reaction of various substituted 2-(vinylphosphoryloxy)benzaldehydes with pyrazolidin-3-one took place at room temperature. Three new bonds (C–C, 2 × C–N) and two new nitrogen and phosphorus heterocycles were simultaneously constructed. The reaction is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.

scholarly journals Multi-Catalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols

2021 ◽  
Author(s):  
Alessandra Casnati ◽  
Dawid Lichosyt ◽  
Bruno Lainer ◽  
Lukas Veth ◽  
Pawel Dydio
Keyword(s):  
Stereoselective Synthesis ◽  
Value Added ◽  
Cross Reactivity ◽  
Transition Metal Catalysts ◽  
Allylic Alcohols ◽  
One Pot ◽  
Benzylic Alcohols ◽  
Material Efficiency ◽  
The One ◽  
High Stereoselectivity

One-pot multi-step procedures bear the potential to rapidly build up molecular complexity while avoiding the wasteful and costly isolations and purifications of consecutive intermediates. Here we report multi-catalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Because each transformation of the sequence is executed by an independent catalyst, without any catalytic cross-reactivity, allylic alcohols bearing a prochiral double bond can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er and >20:1 dr). Overall, with the aid of up to four catalysts operating in a single vessel, the protocols directly convert simple starting materials into a range of value-added products with high stereocontrol and excellent material efficiency, demonstrating both the efficacy and the advantages of the one-pot synthesis employing multiple transition-metal catalysts.

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