Construction of thiazines and oxathianes via [3 + 3] annulation of N-tosylaziridinedicarboxylates and oxiranes with 1,4-dithiane-2,5-diol: application towards the synthesis of bioactive molecules

2017 ◽  
Vol 15 (24) ◽  
pp. 5182-5190 ◽  
Author(s):  
Rohit Kumar Varshnaya ◽  
Prabal Banerjee
Keyword(s):  
Lewis Acid ◽  
Bioactive Molecules ◽  
Efficient Construction

Efficient construction of functionalized thiazine and oxathiane derivatives via [3 + 3] annulation of N-tosylaziridinedicarboxylates and oxiranes with in situ generated mercaptoaldehyde in the presence of a Lewis acid is described.

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>

Reductive Cleavage of Secondary Sulfonamides: Converting Terminal Functional Groups into Versatile Synthetic Handles

2019 ◽  
Author(s):  
Patrick Fier ◽  
Suhong Kim ◽  
Kevin M. Maloney
Keyword(s):  
Functional Groups ◽  
Late Stage ◽  
Reductive Cleavage ◽  
Bioactive Molecules ◽  
General Method

Sulfonamides are pervasive in drugs and agrochemicals, yet are typically considered as terminal functional groups rather than synthetic handles. To enable the general late-stage functionalization of secondary sulfonamides, we have developed a mild and general method to reductively cleave the N-S bonds of sulfonamides to generate sulfinates and amines, components which can further react <i>in-situ</i> to access a variety of other medicinally relevant functional groups. The utility of this platform is highlighted by the selective manipulation of several complex bioactive molecules.

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

scholarly journals PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

2021 ◽  
pp. 174751982098753
Author(s):  
Xiaofang Wu ◽  
Lei Zhou ◽  
Fangshao Li ◽  
Jing Xiao
Keyword(s):  
Acid Chloride ◽  
Bioactive Molecules ◽  
Mechanistic Studies ◽  
One Pot ◽  
Tert Butyl ◽  
Butyl Esters

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

scholarly journals Novel hydrogen chemisorption properties of amorphous ceramic compounds consisting of p-block elements: exploring Lewis acid-base Al–N pair site formed in-situ within polymer-derived silicon-aluminum-nitrogen-based system

2021 ◽  
Author(s):  
Shotaro Tada ◽  
Norifumi Asakuma ◽  
Shiori Ando ◽  
Toru Asaka ◽  
Yusuke Daiko ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Active Site ◽  
Hydrogen Chemisorption ◽  
Acid Base ◽  
Polymer Derived Ceramics ◽  
System P ◽  
Ceramic Compounds ◽  
The Relationship

This paper reports on the relationship between the H2 chemisorption properties and reversible structural reorientation of the possible active site around Al formed in-situ within polymer-derived ceramics (PDCs) based on...

Lewis acid-catalyzed tandem cyclization of in situ generated o-quinone methides and arylsulfonyl hydrazides for a one-pot entry to 3-sulfonylbenzofurans

2019 ◽  
Vol 6 (24) ◽  
pp. 3929-3933 ◽  
Author(s):  
Fan-Xiao Meng ◽  
Ruo-Nan Wang ◽  
Hong-Li Huang ◽  
Shu-Wen Gong ◽  
Qian-Li Li ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Quinone Methides ◽  
One Pot ◽  
Acid Catalyzed ◽  
Tandem Cyclization ◽  
First Time

Lewis acid-mediated one-pot tandem cyclization of o-QMs with arylsulfonyl hydrazides was described for the first time and the corresponding 3-sulfonylbenzofuran products were obtained in moderate to good yields.

Role of the Surface Lewis Acid and Base Sites in the Adsorption of CO2 on Titania Nanotubes and Platinized Titania Nanotubes: An in Situ FT-IR Study

2013 ◽  
Vol 117 (24) ◽  
pp. 12661-12678 ◽  
Author(s):  
Kaustava Bhattacharyya ◽  
Alon Danon ◽  
Baiju K.Vijayan ◽  
Kimberly A. Gray ◽  
Peter C. Stair ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Titania Nanotubes ◽  
Acid And Base ◽  
Ft Ir ◽  
Ir Study ◽  
Adsorption Of Co2 ◽  
Lewis Acid And Base

A novel shape-stabilization strategy for phase change thermal energy storage

2019 ◽  
Vol 7 (14) ◽  
pp. 8194-8203 ◽  
Author(s):  
Changhui Liu ◽  
Ze Xu ◽  
Yan Song ◽  
Peizhao Lv ◽  
Jiateng Zhao ◽  
...  
Keyword(s):  
Energy Storage ◽  
Phase Change ◽  
Phase Change Material ◽  
Lewis Acid ◽  
Thermal Energy ◽  
Thermal Energy Storage ◽  
Acid Catalysis ◽  
Crosslinked Polystyrene ◽  
Change Material

A novel Lewis acid catalysis induced in situ phase change material (PCM) shape-stabilization strategy was developed to fabricate hyper-crosslinked polystyrene (HCPS) encapsulated PCMs towards highly efficient thermal energy storage.

Lewis acids in situ modulate pyridazine-imine Ni catalysed ethylene (co)polymerisation

2019 ◽  
Vol 43 (34) ◽  
pp. 13630-13634 ◽  
Author(s):  
Guohong Wang ◽  
Min Li ◽  
Wenmin Pang ◽  
Min Chen ◽  
Chen Tan
Keyword(s):  
Electron Density ◽  
Lewis Acid ◽  
Lewis Acids ◽  
Acid Base ◽  
Base Interaction ◽  
Acid Base Interaction

The Lewis acid-base interaction between B(iii) Lewis acids and the pyridazine moiety reduced the electron density from the Ni center and in situ modulated the pyridazine-imine nickel catalyzed ethylene (co)polymerisation.

scholarly journals A three-component, Zn(OTf)2-mediated entry into trisubstituted 2-aminoimidazoles

2019 ◽  
Vol 15 ◽  
pp. 1061-1064 ◽  
Author(s):  
Alexei Lukin ◽  
Anna Bakholdina ◽  
Anna Kryukova ◽  
Alexander Sapegin ◽  
Mikhail Krasavin
Keyword(s):  
Lewis Acid ◽  
Primary Amine ◽  
Three Component Reaction ◽  
Acid Catalyzed ◽  
In Situ Generation

A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)2-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported base-promoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.

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