Stereoselective Construction of Pyrazinoindoles and Oxazinoindoles via Ring-Opening/Pictet-Spengler Reaction of Aziridines and Epoxides with 3-Methylindoles and Carbonyls

Imtiyaz Ahmad Wani, Subhomoy Das, Shobhan Mondal, Manas K. Ghorai

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

A highly efficient and stereoselective route to access 1,3-disubstituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles and 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indoles with excellent stereoselectivity (de, ee >99%) via base mediated ring opening of aziridines/epoxides with 3-methylindoles followed by BF 3 ·OEt 2 catalyzed Pictet-Spengler reaction is accomplished. Interestingly, PTSA promoted cyclization led to the formation of oxidized 3,4-dihydropyrazino[1,2-a]indoles in excellent yields via an unprecedented Pictet-Spengler-detosylation cascade.

Original languageEnglish
Pages (from-to)14553-14567
Number of pages15
JournalJournal of Organic Chemistry
Volume83
Issue number23
DOIs
StatePublished - 7 Dec 2018
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

Fingerprint

Dive into the research topics of 'Stereoselective Construction of Pyrazinoindoles and Oxazinoindoles via Ring-Opening/Pictet-Spengler Reaction of Aziridines and Epoxides with 3-Methylindoles and Carbonyls'. Together they form a unique fingerprint.

Cite this