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Stereodivergent Synthesis of Trisubstituted Enamides: Direct Access to Both Pure Geometrical Isomers

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journal contribution
posted on 09.10.2019, 17:34 by Luca Massaro, Jianping Yang, Suppachai Krajangsri, Emanuele Silvi, Thishana Singh, Pher G. Andersson
A stereodivergent strategy has been developed to access either (E)- or (Z)-isomers of trisubstituted enamides. Starting from an extensive range of ketones, it was possible to synthesize and isolate the desired pure isomer by switching the reaction conditions. Lewis acid activation enables the formation of the (E)-isomers in high stereoselectivity (>90:10) and good yields. On the other hand, the use of a Brønsted acid allows the preparation of the (Z)-isomers, again in high selectivity (up to 99:1), with moderate yields.