A Synthetic Route to Chiral 1,4-Disubstituted Tetrahydro-β-Carbolines via Domino Ring-Opening Cyclization of Activated Aziridines with 2-Vinylindoles

Masthanvali Sayyad; Imtiyaz Ahmad Wani; Raja Babu; Yerramsetti Nanaji; Manas K Ghorai

doi:10.1021/acs.joc.6b02719

A Synthetic Route to Chiral 1,4-Disubstituted Tetrahydro-β-Carbolines via Domino Ring-Opening Cyclization of Activated Aziridines with 2-Vinylindoles

J Org Chem. 2017 Mar 3;82(5):2364-2374. doi: 10.1021/acs.joc.6b02719. Epub 2017 Feb 22.

Authors

Masthanvali Sayyad¹, Imtiyaz Ahmad Wani¹, Raja Babu¹, Yerramsetti Nanaji¹, Manas K Ghorai¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.

PMID: 28186754
DOI: 10.1021/acs.joc.6b02719

Abstract

A simple and efficient strategy for the synthesis of various 1,4-disubstituted tetrahydro-β-carbolines with excellent stereoselectivity (de, ee up to >99%) via domino ring opening cyclization (DROC) of activated aziridines with 2-vinylindoles is described. The reaction proceeds through LiClO₄-catalyzed Friedel-Crafts-type alkylation of 2-vinylindoles with activated aziridines followed by an intramolecular aza-Michael reaction in a domino fashion.

Publication types

Research Support, Non-U.S. Gov't