scholarly journals Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis

2011 ◽  
Vol 7 ◽  
pp. 1315-1322 ◽  
Author(s):  
Inhee Cho ◽  
Labros Meimetis ◽  
Lee Belding ◽  
Michael J Katz ◽  
Travis Dudding ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Ligand ◽  
One Pot ◽  
Rapid Access ◽  
Short Synthesis ◽  
The One

A variety of ortho,ortho'-disubstituted hydrobenzoin derivatives are readily accessible through a directed ortho,ortho'-dimetalation strategy in which the alcohol functions in hydrobenzoin are deprotonated by n-BuLi and the resulting lithium benzyl alkoxides serve as directed metalation groups. The optimization and scope of this reaction are discussed, and the utility of this process is demonstrated in the one-pot preparation of a number of chiral diols as well as a short synthesis of the chiral ligand Vivol.

The one pot asymmetric synthesis of 3,3′-pyrrolidonyl spiroxindoles via a regio- and stereoselective domino reaction

2019 ◽  
Vol 17 (35) ◽  
pp. 8140-8148
Author(s):  
Saumen Hajra ◽  
Suhas Shivajirao Bhosale ◽  
Atanu Hazra ◽  
Nikhil Kanaujia
Keyword(s):  
Asymmetric Synthesis ◽  
Domino Reaction ◽  
One Pot ◽  
The One

The asymmetric synthesis of 4-aryl-3,3′-spiropyrrolidonyl oxindoles with excellent stereoselectivity (dr >99 : 1 and an ee up to >99%) was achieved via a domino reaction.

Bench-stable imine surrogates for the one-pot and catalytic asymmetric synthesis of α-amino esters/ketones

2020 ◽  
Vol 56 (91) ◽  
pp. 14243-14246
Author(s):  
Huacheng Xu ◽  
Adila Nazli ◽  
Cheng Zou ◽  
Zhi-Peng Wang ◽  
Yun He
Keyword(s):  
Asymmetric Synthesis ◽  
One Pot ◽  
Amino Esters ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric ◽  
The One

An unpresented catalytic asymmetric method for the synthesis of α-amino esters and ketones from novel imine surrogates is reported.

scholarly journals Microwave - Assisted Synthesis of a Library of Pyrrolo[1,2-c]quinazolines

2019 ◽  
Vol 70 (9) ◽  
pp. 3094-3099 ◽  
Author(s):  
Emilian Georgescu ◽  
Florea Dumitrascu ◽  
Florentina Georgescu ◽  
Constantin Draghici ◽  
Denisa Dumitrescu
Keyword(s):  
Large Range ◽  
Dipolar Cycloaddition ◽  
Microwave Assisted Synthesis ◽  
One Pot ◽  
Synthetic Pathway ◽  
Microwave Assisted ◽  
Rapid Access ◽  
Quinazoline Derivatives ◽  
The One

A library of new pyrrolo[1,2-c]quinazoline derivatives was obtained by the one-pot, three-component microwave-assisted synthesis, starting from quinazolines, 2-bromoacetyl derivatives and electron-deficient alkynes in 1,2-epoxybutane via 1,3-dipolar cycloaddition of quinazolinium N-ylides. This synthetic pathway offers a simple and rapid access to a large range of pyrrolo[1,2-c]quinazoline derivatives.

New regio-, stereo-, diastereo- and enantioselective one-pot reactions mediated by organometallic derivatives

2004 ◽  
Vol 76 (3) ◽  
pp. 517-535 ◽  
Author(s):  
Nicka Chinkov ◽  
G. Sklute ◽  
Helena Chechik ◽  
Adi Abramovitch ◽  
Deborah Amsallem ◽  
...  
Keyword(s):  
Double Bond ◽  
Asymmetric Synthesis ◽  
Potential Application ◽  
Bond Activation ◽  
Chiral Center ◽  
Elimination Reaction ◽  
One Pot ◽  
Carbon Carbon Bonds ◽  
New Strategy ◽  
The One

In the first part of the lecture, we will discuss the one-pot preparation of chiral homoallylic alcohol and amine derivatives by a copper-catalyzed four-component reaction. In this process, three new carbon-carbon bonds as well as a quaternary and a tertiary chiral center are created with excellent regio- and diastereoselectivities. When the reaction was performed without adding external electrophiles, a β-elimination reaction took place to give polysubstituted allenes in good overall yields. This strategy of zinc-homologation followed by a β-elimination reaction was also synthetically used for the transformation of sp3 sulfoxides into olefins with potential application in asymmetric synthesis. Finally, in the second part of this lecture, the stereoselective preparation of metallated dienes in only two chemical steps from commercially available products will be described. This new strategy is based on a tandem allylic C-H bond activation of a remote ω-double bond followed by an elimination reaction.

Rapid access to indole-fused bicyclo[2.2.2]octanones by merging the umpolung strategy and molecular iodine as a green catalyst

2020 ◽  
Vol 18 (22) ◽  
pp. 4193-4197 ◽  
Author(s):  
Takumi Abe ◽  
Seiya Hirao
Keyword(s):  
Molecular Iodine ◽  
One Pot ◽  
Green Catalyst ◽  
Rapid Access ◽  
The One

We have achieved the one-pot construction of otherwise more difficult to access indole-fused bicyclo[2.2.2]octanones by merging the umpolung strategy and molecular iodine catalyst.

Asymmetric Synthesis of Cyclopentene-Fused Tetrahydroquinolines via N-Heterocyclic Carbene Catalyzed Domino Reactions

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2523-2532 ◽  
Author(s):  
Long Zhao ◽  
Sun Li ◽  
Lei Wang ◽  
Shun Yu ◽  
Gerhard Raabe ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Domino Reactions ◽  
One Pot ◽  
New Strategy ◽  
The One

A new strategy for the N-heterocyclic carbene catalyzed asymmetric synthesis of cyclopentene-fused tetrahydroquinoline derivatives has been developed. The one-pot organocatalytic domino protocol allows a direct entry to the characteristic cyclopenta[c]tetrahydroquinoline core of many alkaloids and some potential drugs employing readily available quinolinone and enal substrates in good domino yields and stereoselectivities.

A Series of Metal-Organic Frameworks for Selective CO2 Capture and Catalytic Oxidative Carboxylation of Olefins

2018 ◽  
Author(s):  
Huong T. D. Nguyen ◽  
Y B. N. Tran ◽  
Hung N. Nguyen ◽  
Tranh C. Nguyen ◽  
Felipe Gándara ◽  
...  
Keyword(s):  
Room Temperature ◽  
Gas Adsorption ◽  
New Materials ◽  
One Pot ◽  
Acid Gas ◽  
Naphthalene Diimide ◽  
Styrene Carbonate ◽  
Metal Organic ◽  
Adsorption Of Co ◽  
The One

<p>Three novel lanthanide metal˗organic frameworks (Ln-MOFs), namely MOF-590, -591, and -592 were constructed from a naphthalene diimide tetracarboxylic acid. Gas adsorption measurements of MOF-591 and -592 revealed good adsorption of CO<sub>2</sub> (low pressure, at room temperature) and moderate CO<sub>2</sub> selectivity over N<sub>2</sub> and CH<sub>4</sub>. Accordingly, breakthrough measurements were performed on a representative MOF-592, in which the separation of CO<sub>2</sub> from binary mixture containing N<sub>2</sub> and CO<sub>2</sub> was demonstrated without any loss in performance over three consecutive cycles. Moreover, MOF-590, MOF-591, and MOF-592 exhibited catalytic activity in the one-pot synthesis of styrene carbonate from styrene and CO<sub>2</sub> under mild conditions (1 atm CO<sub>2</sub>, 80 °C, and solvent-free). Among the new materials, MOF-590 revealed a remarkable efficiency with exceptional conversion (96%), selectivity (95%), and yield (91%). </p><br>

A Short Synthesis of (+)-Brefeldin C via Enantioselective Radical Hydroalkynylation

2019 ◽  
Author(s):  
Lars Gnägi ◽  
Severin Vital Martz ◽  
Daniel Meyer ◽  
Robin Marc Schärer ◽  
Philippe Renaud
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Oxidation State ◽  
Single Step ◽  
Radical Process ◽  
Target Molecule ◽  
Short Synthesis ◽  
The One

<div><div><div><div><p>A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows to achieve a high trans diastereoselectivity during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis require six product purifications and it provides (+)-brefeldin C in 18% overall yield.</p></div></div></div></div>

A Study on the Rearrangement of Dialkyl 1-Aryl-1-hydroxymethylphosphonates to Benzyl Phosphates

2020 ◽  
Vol 24 (4) ◽  
pp. 465-471 ◽  
Author(s):  
Zita Rádai ◽  
Réka Szabó ◽  
Áron Szigetvári ◽  
Nóra Zsuzsa Kiss ◽  
Zoltán Mucsi ◽  
...  
Keyword(s):  
Quantum Chemical ◽  
Room Temperature ◽  
Phase Transfer ◽  
One Pot ◽  
Substrate Dependence ◽  
Triethylbenzylammonium Chloride ◽  
One Step ◽  
The Pudovik Reaction ◽  
The One ◽  
Solid Liquid

The phospha-Brook rearrangement of dialkyl 1-aryl-1-hydroxymethylphosphonates (HPs) to the corresponding benzyl phosphates (BPs) has been elaborated under solid-liquid phase transfer catalytic conditions. The best procedure involved the use of triethylbenzylammonium chloride as the catalyst and Cs2CO3 as the base in acetonitrile as the solvent at room temperature. The substrate dependence of the rearrangement has been studied, and the mechanism of the transformation under discussion was explored by quantum chemical calculations. The key intermediate is an oxaphosphirane. The one-pot version starting with the Pudovik reaction has also been developed. The conditions of this tandem transformation were the same, as those for the one-step HP→BP conversion.

An Overview of the One-pot Synthesis of Imidazolines

2020 ◽  
Vol 24 (20) ◽  
pp. 2341-2355
Author(s):  
Thaipparambil Aneeja ◽  
Sankaran Radhika ◽  
Mohan Neetha ◽  
Gopinathan Anilkumar
Keyword(s):  
Asymmetric Catalysis ◽  
Organic Compounds ◽  
Ring Opening ◽  
Ecological Impact ◽  
Chiral Auxiliary ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One ◽  
Synthetic Intermediate ◽  
Heterocyclic Moiety

One-pot syntheses are a simple, efficient and easy methodology, which are widely used for the synthesis of organic compounds. Imidazoline is a valuable heterocyclic moiety used as a synthetic intermediate, chiral auxiliary, chiral catalyst and a ligand for asymmetric catalysis. Imidazole is a fundamental unit of biomolecules that can be easily prepared from imidazolines. The one-pot method is an impressive approach to synthesize organic compounds as it minimizes the reaction time, separation procedures, and ecological impact. Many significant one-pot methods such as N-bromosuccinimide mediated reaction, ring-opening of tetrahydrofuran, triflic anhydrate mediated reaction, etc. were reported for imidazoline synthesis. This review describes an overview of the one-pot synthesis of imidazolines and covers literature up to 2020.

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