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

Luca Massaro | Zendy; Jianping Yang | Zendy; Suppachai Krajangsri | Zendy; Emanuele Silvi | Zendy; Thishana Singh | Zendy; Pher G. Andersson | Zendy

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

Author(s) -

Luca Massaro,

Jianping Yang,

Suppachai Krajangsri,

Emanuele Silvi,

Thishana Singh,

Pher G. Andersson

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b01803

Subject(s) - chemistry , stereoselectivity , selectivity , lewis acids and bases , combinatorial chemistry , stereoisomerism , reaction conditions , cis–trans isomerism , brønsted–lowry acid–base theory , stereochemistry , organic chemistry , catalysis

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.

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