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.

ChemInform Abstract: A Novel and Efficient Domino Reaction for the One-Pot Synthesis of Spiro-2-aminopyrimidinones.

ChemInform ◽  
2008 ◽  
Vol 39 (40) ◽  
Author(s):  
Sorour Ramezanpour ◽  
Mehri Seyed Hashtroudi ◽  
Hamid Reza Bijanzadeh ◽  
Saeed Balalaie
Keyword(s):  
Domino Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One

ChemInform Abstract: Asymmetric Synthesis of Tetrahydropyridines via an Organocatalytic One-Pot Multicomponent Michael/Aza-Henry/Cyclization Triple Domino Reaction.

ChemInform ◽  
2015 ◽  
Vol 46 (18) ◽  
pp. no-no
Author(s):  
Marcus Bluemel ◽  
Pankaj Chauhan ◽  
Robert Hahn ◽  
Gerhard Raabe ◽  
Dieter Enders
Keyword(s):  
Asymmetric Synthesis ◽  
Domino Reaction ◽  
One Pot

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 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.

scholarly journals Asymmetric Synthesis of Tetrahydropyridines via an Organocatalytic One-Pot Multicomponent Michael/Aza-Henry/Cyclization Triple Domino Reaction

2014 ◽  
Vol 16 (22) ◽  
pp. 6012-6015 ◽  
Author(s):  
Marcus Blümel ◽  
Pankaj Chauhan ◽  
Robert Hahn ◽  
Gerhard Raabe ◽  
Dieter Enders
Keyword(s):  
Asymmetric Synthesis ◽  
Domino Reaction ◽  
One Pot

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.

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.

scholarly journals Multicomponent Domino Reaction in the Asymmetric Synthesis of Cyclopentan[c]pyran Core of Iridoid Natural Products

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1308
Author(s):  
Alejandro Manchado ◽  
Victoria Elena Ramos ◽  
David Díez ◽  
Narciso M. Garrido
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Asymmetric Synthesis ◽  
Heteronuclear Nmr ◽  
Domino Reaction ◽  
One Pot ◽  
Pharmaceutical Development ◽  
New Drug ◽  
Anti Inflammatory ◽  
Pharmaceutical Properties

The asymmetric synthesis of a compound with the cyclopentan[c]pyran core of iridoid natural products in four steps and 40% overall yield is reported. Our methodology includes a one-pot tandem domino reaction which provides a trisubstituted cyclopentane with five new completely determined stereocenters, which were determined through 2D homo and heteronuclear NMR and n.O.e. experiments on different compounds specially designed for this purpose, such as a dioxane obtained from a diol. Due to their pharmaceutical properties, including sedative, analgesic, anti-inflammatory, CNS depressor or anti-conceptive effects, this methodology to produce the abovementioned iridoid derivatives, is an interesting strategy in terms of new drug discovery as well as pharmaceutical development.

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