Catalyst-Free Synthesis of Polycyclic Spiroindolines by Cascade Reaction of 3-(2-Isocyanoethyl)indoles with 1-Sulfonyl-1,2,3-triazoles

Chen, Cong; Chen, Jing; Wang, Han; Xu, Zefeng; Duan, Shengguo; Li, Chuan‐Ying

doi:10.1021/acs.joc.3c00800

Cited by 3 publications

(1 citation statement)

References 66 publications

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“…The chiral phosphoric acid catalyst PA2-PA7 used was synthesized according to the established literature procedure . β,γ-Alkynyl-α-imino esters ( 1a – r ), tryptamines ( 2a – q ), alkynyl trifluoromethyl ketimine 4 , and N a -protected tryptamine 2′ were prepared according to the modified literature procedures. , Tryptophol 2r is commercially available. All reactions were carried out in oven-dried glassware with magnetic stirring.…”

Section: Methodsmentioning

confidence: 99%

Asymmetric Cascade Dearomatization–Cyclization Reaction of Tryptamines with β,γ-Alkynyl-α-imino Esters: Access to Hexahydropyrrolo[2,3-b]indole-Containing Tetrasubstituted α-Amino Allenoates

Khajuria,

Saini,

Subba

et al. 2024

J. Org. Chem.

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An organocatalytic enantio- and diastereoselective synthesis of hexahydropyrrolo[2,3-b]indole-containing tetrasubstituted α-amino allenoates, exhibiting both axial and central chirality, has been accomplished via cascade dearomatization–cyclization reaction. The γ-addition to β,γ-alkynyl-α-imino esters provides a library of densely substituted highly enantioenriched allenes in high yields and excellent stereoselectivities. In addition, the scope of this methodology has been extended to tryptophol as well. A scale-up reaction and synthetic transformations of the products were performed to demonstrate the practical usefulness of this approach.

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Section: Methodsmentioning

confidence: 99%

Asymmetric Cascade Dearomatization–Cyclization Reaction of Tryptamines with β,γ-Alkynyl-α-imino Esters: Access to Hexahydropyrrolo[2,3-b]indole-Containing Tetrasubstituted α-Amino Allenoates

Khajuria,

Saini,

Subba

et al. 2024

J. Org. Chem.

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Visible‐Light‐Induced Diastereoselective Cascade Cyclization to Construct Polycyclic Spiroindolines

Ranga Rao,

Shiva Prasad,

Ravi

et al. 2024

Adv Synth Catal

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We herein reported, a visible‐light‐induced K2S2O8 mediated cascade reaction of 3‐(2‐isocyanoethyl)indoles with α‐oxocarboxylic acids leading to diastereoselective synthesis of polycyclic spiroindolines bearing an N‐formyl unit derivative utilising the alkali metal salt K2S2O8 as a catalyst under mild reaction conditions. This study offers an illustration of α‐oxocarboxylic acids and 3‐(2‐isocyanoethyl)indoles‐based reactions as it shows the involvement of glyoxolate ions without decarboxylation to access polycyclic spiroindoles bearing an N‐formyl unit analogue. The batch process can be extended to a continuous flow system using a glass tube loaded with K2S2O8 placed between the PFA capillary reactor, which can greatly advance the reaction efficiency and can even be promoted to gram‐scale synthesis.

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Diastereocontrolled Construction of Spiroindolenines via Hexafluoroisopropanol-Promoted Dearomative Epoxide–Indole Cyclization

Chouhan,

Bhattacharyya,

Das

2024

Org. Lett.

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Herein, we report the discovery of the ipso-selective, dearomatizing spirocyclization of indole-tethered epoxides as a fundamentally new approach for constructing spiroindolenines equipped with three contiguous stereogenic centers under complete diastereocontrol (dr >99:1) and in high yields. Promoted by hexafluoroisopropanol, the protocol features a broad substrate scope, easy scale-up, and versatile transformations of the synthesized spiroindolenines.

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Catalyst-Free Synthesis of Polycyclic Spiroindolines by Cascade Reaction of 3-(2-Isocyanoethyl)indoles with 1-Sulfonyl-1,2,3-triazoles

Cited by 3 publications

References 66 publications

Asymmetric Cascade Dearomatization–Cyclization Reaction of Tryptamines with β,γ-Alkynyl-α-imino Esters: Access to Hexahydropyrrolo[2,3-b]indole-Containing Tetrasubstituted α-Amino Allenoates

Asymmetric Cascade Dearomatization–Cyclization Reaction of Tryptamines with β,γ-Alkynyl-α-imino Esters: Access to Hexahydropyrrolo[2,3-b]indole-Containing Tetrasubstituted α-Amino Allenoates

Visible‐Light‐Induced Diastereoselective Cascade Cyclization to Construct Polycyclic Spiroindolines

Diastereocontrolled Construction of Spiroindolenines via Hexafluoroisopropanol-Promoted Dearomative Epoxide–Indole Cyclization

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