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

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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… Click to show full 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.

Keywords: lewis acid; catalysed asymmetric; cyclopropyl; asymmetric cascade; cyclopropyl ketones; acid catalysed

Journal Title: Chemical communications
Year Published: 2020

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