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Lewis acid catalysed asymmetric cascade reaction of cyclopropyl ketones: concise synthesis of pyrrolobenzothiazoles

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Abstract

Utilizing the C4 reactive site of cyclopropyl ketones and a chiral N,N′-dioxide-scandium(III) complex as a catalyst, a concise ring-opening/cyclization/thio-Michael cascade method was developed for the synthesis of chiral benzothiazole derivatives from a simple 2-aminothiophenol material. The kinetic resolution and the origin of stereoselectivity were elucidated via a possible catalytic model.

Graphical abstract: Lewis acid catalysed asymmetric cascade reaction of cyclopropyl ketones: concise synthesis of pyrrolobenzothiazoles

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Article information


Submitted
20 Aug 2020
Accepted
28 Sep 2020
First published
28 Sep 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Lewis acid catalysed asymmetric cascade reaction of cyclopropyl ketones: concise synthesis of pyrrolobenzothiazoles

F. Chang, B. Shen, S. Wang, L. Lin and X. Feng, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC05667G

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