Research data supporting "Combination of enabling technologies to improve and describe the stereoselectivity of Wolff-Staudinger cascade reaction"

Abstract

A new single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of alpha-diazoketones at high temperature. A number of amides and beta-lactams were obtained by in situ ketene generation and reaction with amines and imines respectively in good to excellent yields. The preferential formation of trans-configured beta-lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported and a new web-based molecular viewer, which takes advantage from augmented reality (AR) technology, is also described for a faster interpretation of computed data.EPSRC [EP/K009494/1, EP/K039520/1 and EP/M004120/1

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