An efficient synthetic route to carbocyclic enaminonitriles via Lewis acid catalysed domino-ring-opening-cyclisation (DROC) of donor–acceptor cyclopropanes with malononitrile

A novel synthetic route to functionalized indolinesviaLewis acid catalyzed ring-opening of activated aziridines followed by Cu(OAc)2-mediated intramolecular C–H amination in one-pot with excellent enantio- and diastereospecificity (ee 99%; de >99%).

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An iron-catalyzed domino reaction of donor–acceptor cyclopropanes: a diastereoselective approach towards diversely functionalized pyrrolo-quinazolines

Organic & Biomolecular Chemistry ◽

10.1039/d1ob02215f ◽

2022 ◽

Author(s):

Samiran Dhara ◽

Subhadeep Ghosh ◽

Asish R. Das

Keyword(s):

Ring Opening ◽

Domino Reaction ◽

Synthetic Route ◽

Aniline Derivatives ◽

Donor Acceptor

An expeditious synthetic route to access functionalized pyrrolo[2,1-b]quinazoline scaffolds has been achieved via domino ring opening cyclization (DROC) reactions of donor–acceptor (D–A) cyclopropanes and 2-amino(methyl)aniline derivatives.

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Stereoselective synthesis of 3-spiropiperidino indoleninesviaSN2-type ring opening of activated aziridines with 1H-indoles/Pd-catalyzed spirocyclization with propargyl carbonates

Chemical Communications ◽

10.1039/c8cc04249g ◽

2018 ◽

Vol 54 (62) ◽

pp. 8583-8586 ◽

Cited By ~ 11

Author(s):

Sajan Pradhan ◽

Chandan Kumar Shahi ◽

Aditya Bhattacharyya ◽

Manas K. Ghorai

Keyword(s):

Lewis Acid ◽

Ring Opening ◽

Stereoselective Synthesis ◽

Synthetic Route ◽

Acid Catalyzed ◽

High Yields

A novel synthetic route to 3-spiropiperidino indoleninesviaLewis acid catalyzed SN2-type ring opening of activated aziridines with 1H-indoles followed by Pd-catalyzed spirocyclization with propargyl carbonates in high yields (up to 88%) with excellent diastereo- and enantiospecificity (dr >99 : 1; ee up to >99) is reported.

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Lewis Acid Catalyzed Nucleophilic Ring Opening and 1,3-Bisfunctionalization of Donor–Acceptor Cyclopropanes with Hydroperoxides: Access to Highly Functionalized Peroxy/(α-Heteroatom Substituted)Peroxy Compounds

The Journal of Organic Chemistry ◽

10.1021/acs.joc.8b02561 ◽

2018 ◽

Vol 84 (2) ◽

pp. 710-725 ◽

Cited By ~ 13

Author(s):

Kuldeep Singh ◽

Tishyasoumya Bera ◽

Vandana Jaiswal ◽

Subrata Biswas ◽

Biplab Mondal ◽

...

Keyword(s):

Lewis Acid ◽

Ring Opening ◽

Donor Acceptor ◽

Acid Catalyzed ◽

Peroxy Compounds ◽

Nucleophilic Ring Opening

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A Metathetic Approach to [5/5/6] Aza-Tricyclic Core of Dendrobine, Kopsanone, and Lycopalhine A Type of Alkaloids

Synthesis ◽

10.1055/s-0039-1690620 ◽

2019 ◽

Vol 51 (21) ◽

pp. 3981-3988 ◽

Cited By ~ 2

Author(s):

Sambasivarao Kotha ◽

Sunil Pulletikurti

Keyword(s):

Lewis Acid ◽

Ring Opening ◽

Synthetic Approach ◽

Synthetic Route ◽

Ring Closing Metathesis ◽

Tricyclic Core

A concise synthetic approach to [5/5/6] tricyclic pyrrolidine core of dendrobine is reported. This methodology relies on the construction of β-hydroxylactams by NaBH4-I2 reduction followed by reaction of allylsilane with the aid of Lewis acid to generate alkenyl lactams in good yields. Further, ring-opening metathesis (ROM) followed by ring-closing metathesis (RCM) were used to assemble the [5/5/6] aza-tricyclic skeleton of dendrobine. This short synthetic route has been expanded to assemble tricyclic [5/5/8] system with pentenylboronic acid.

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