Synthesis of cinchona alkaloid sulfonamide polymers as sustainable catalysts for the enantioselective desymmetrization of cyclic anhydrides

RSC Advances ◽  
2016 ◽  
Vol 6 (76) ◽  
pp. 72300-72305 ◽  
Author(s):  
Shohei Takata ◽  
Yuta Endo ◽  
Mohammad Shahid Ullah ◽  
Shinichi Itsuno
Keyword(s):  
Cinchona Alkaloid ◽  
High Yield ◽  
Chiral Polymers ◽  
Cyclic Anhydrides

Mizoroki–Heck polymerization of cinchona sulfonamide gave chiral polymers, which are active catalysts for enantioselective desymmetrization of cyclic anhydrides to give chiral hemiesters in high yield with high enantioselectivities.

Asymmetric chlorination of 4-substituted pyrazolones catalyzed by natural cinchona alkaloid

2016 ◽  
Vol 52 (76) ◽  
pp. 11426-11429 ◽  
Author(s):  
Xiaoze Bao ◽  
Shiqiang Wei ◽  
Liwei Zou ◽  
Yuli He ◽  
Fuzhao Xue ◽  
...  
Keyword(s):  
Cinchona Alkaloid ◽  
High Yield

A natural quinidine catalyzed asymmetric chlorination of 4-substituted pyrazolones was revealed in high yield and excellent enantioselectivity.

Cinchona Alkaloid Catalyzed Asymmetric Desymmetrization ofmeso-Cyclic Anhydrides: The Origins of Stereoselectivity

ChemCatChem ◽  
2015 ◽  
Vol 7 (24) ◽  
pp. 4173-4179 ◽  
Author(s):  
Burcu Dedeoglu ◽  
Saron Catak ◽  
Asli Yildirim ◽  
Carsten Bolm ◽  
Viktorya Aviyente
Keyword(s):  
Cinchona Alkaloid ◽  
Cyclic Anhydrides

scholarly journals Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions

2015 ◽  
Vol 6 (2) ◽  
pp. 1350-1354 ◽  
Author(s):  
Alejandro Cabanillas ◽  
Christopher D. Davies ◽  
Louise Male ◽  
Nigel S. Simpkins
Keyword(s):  
Michael Addition ◽  
Ring Closure ◽  
Cinchona Alkaloid ◽  
High Yield ◽  
Michael Additions

Alkaloid catalysed additions to triketopiperazines gives products in high yield and er (88 : 12 to 99 : 1), including bridged hydroxy-DKPs via Michael-addition–ring closure.

Cinchona Alkaloid Derivatives modified Fe3O4 Nanoparticles for Enantioselective Ring Opening of meso- Cyclic Anhydrides

2022 ◽  
Author(s):  
Hemant P. Soni ◽  
Sanjiv O. Tomer
Keyword(s):  
Carboxylic Acid ◽  
Fe3o4 Nanoparticles ◽  
Ring Opening ◽  
Acid Group ◽  
Cinchona Alkaloid ◽  
Carboxylic Acid Group ◽  
Cyclic Anhydrides ◽  
Quinoline Moiety ◽  
Molecular Framework ◽  
Long Chain

In the present work, the molecular framework of the quinidine was modified at the methoxy functional of C6’ carbon of quinoline moiety with a long-chain carboxylic acid group (-COOH) and...

scholarly journals ADMET Polymerization of Dimeric Cinchona Squaramides for the Preparation of a Highly Enantioselective Polymeric Organocatalyst

Catalysts ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 591
Author(s):  
Mohammad Shahid Ullah ◽  
Sadia Afrin Chhanda ◽  
Shinichi Itsuno
Keyword(s):  
Second Generation ◽  
Michael Reaction ◽  
Cinchona Alkaloids ◽  
Cinchona Alkaloid ◽  
Acyclic Diene Metathesis ◽  
Chiral Polymers ◽  
Admet Polymerization ◽  
Reaction Condition ◽  
High Yields ◽  
Asymmetric Michael Reaction

Under the acyclic diene metathesis (ADMET) reaction condition, the C3-vinyl groups of cinchona alkaloids readily react with each other to form a C-C bond. A novel type of cinchona alkaloid polymers was synthesized from dimeric cinchona squaramides using the Hoveyda-Grubbs’ second-generation catalysts (HG2) by means of ADMET reaction. The chiral polymers, containing cinchona squaramide moieties in their main chains, were subsequently employed as catalysts for the enantioselective Michael reaction to give the corresponding chiral adducts in high yields with excellent enantioselectivity and diastereoselectivity. Both enantiomers from the asymmetric Michael reaction were distinctively prepared while using the polymeric catalysts, possessing pseudoenantiomeric structures. The catalysts were readily recovered from the reaction mixture and recycled several times due to the insolubility of the cinchona-based squaramide polymers.

Antiviral Bioactivity of Chiral β-Amino Acid Ester Derivatives Synthesized through a One-Pot, Solvent-Free Asymmetric Mannich Reaction

Synlett ◽  
2018 ◽  
Vol 29 (14) ◽  
pp. 1921-1925 ◽  
Author(s):  
Song Bai ◽  
Shan Liu ◽  
Yunying Zhu ◽  
Kunhong Zhao ◽  
Qin Wu
Keyword(s):  
Amino Acid ◽  
Acid Ester ◽  
Antiviral Agent ◽  
Amino Acid Ester ◽  
Solvent Free ◽  
Cinchona Alkaloid ◽  
High Yield ◽  
One Pot ◽  
Solvent Free Conditions

A series of both enantiomers of chiral β-amino acid ester derivatives containing a 4-(piperidin-1-yl)pyrimidine moiety was prepared in high yield and excellent enantioselectivity excess (up to >99% enantiomeric excess) using a chiral cinchona alkaloid thiourea catalyst under one-pot solvent-free conditions. Antiviral bioassay experimental results showed that some of the chiral products exhibited higher antiviral activities against tobacco mosaic virus (TMV) in vivo than the commercial antiviral agent ningnanmycin.

Sign in / Sign up

Export Citation Format

Share Document