Asymmetric synthesis of dihydrocarbazoles through Friedel-Crafts alkylation/annulation sequential reaction of indoles

Chemical Communications ◽

10.1039/d1cc05099k ◽

2021 ◽

Author(s):

Linfeng Hu ◽

Weidi Cao ◽

Kaixuan Wang ◽

Xiaohua Liu ◽

Xiaoming Feng

Keyword(s):

Asymmetric Synthesis ◽

One Pot ◽

Sequential Reaction

An enantioselective tandem Friedel-Crafts alkylation/annulation of indoles with diazoacetoacetate enones is realized in one pot. A series of dihydrocarbazoles were obtained in moderate yields with good to excellent ee values...

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Green One-Pot Asymmetric Synthesis of Peptidomimetics via Sequential Organocatalyzed Aziridination and Passerini Multicomponent Reaction

Synthesis ◽

10.1055/s-0039-1690774 ◽

2019 ◽

Vol 52 (07) ◽

pp. 1076-1086

Author(s):

Deborah A. dos Santos ◽

Allan R. da Silva ◽

Javier Ellena ◽

Cecilia C. P. da Silva ◽

Marcio W. Paixão ◽

...

Keyword(s):

Asymmetric Synthesis ◽

Protease Inhibitors ◽

Multicomponent Reaction ◽

Efficient Method ◽

Cysteine Protease ◽

Heterocyclic Compounds ◽

Solvent Mixture ◽

Cysteine Protease Inhibitors ◽

One Pot ◽

Sequential Reaction

Peptidomimetics containing an aziridine moiety have been reported as potent cysteine protease inhibitors. In this sense, the development of stereoselective and sustainable synthetic strategies to obtain three-membered N-heterocyclic compounds has gained importance in the last decades. In this work, an efficient method was designed to achieve highly functionalized aziridine peptidomimetics via a sequential reaction, which involves the organocatalytic aziridination of α,β-unsaturated aldehydes followed by the Passerini multicomponent reaction in an environmentally friendly solvent mixture (ethanol: water).

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Organocatalytic one-pot asymmetric synthesis of functionalized spiropyrazolones via a Michael-aldol sequential reaction

RSC Advances ◽

10.1039/c6ra13923j ◽

2016 ◽

Vol 6 (81) ◽

pp. 77474-77480 ◽

Cited By ~ 17

Author(s):

Mamatha Amireddy ◽

Kwunmin Chen

Keyword(s):

Asymmetric Synthesis ◽

One Pot ◽

Sequential Reaction ◽

Consecutive Reaction

An efficient organocatalytic method was developed for synthesizing functionalized spiropyrazolone derivatives by using a Michael-aldol consecutive reaction.

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ChemInform Abstract: Organocatalytic One-Pot Asymmetric Synthesis of Functionalized Spiropyrazolones via a Michael-Aldol Sequential Reaction.

ChemInform ◽

10.1002/chin.201652190 ◽

2016 ◽

Vol 47 (52) ◽

Author(s):

Mamatha Amireddy ◽

Kwunmin Chen

Keyword(s):

Asymmetric Synthesis ◽

One Pot ◽

Sequential Reaction

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

Current Organic Chemistry ◽

10.2174/1385272824999200407093625 ◽

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.

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