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Current Organic Synthesis


ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Review Article

Tertiary Enamides: Versatile and Available Substrates in Synthetic Chemistry

Author(s): Xiaohua Cai*, Mengzhi Yang and Hui Guo*

Volume 16, Issue 1, 2019

Page: [70 - 97] Pages: 28

DOI: 10.2174/1570179415666181107122814

Price: $65


Background: Enamines and their variant enamides as powerful and versatile synthons have attracted great attention in synthetic chemistry. Enamides display unique stability and reduce enaminic reactivity in view of the electron-withdrawing effect of N-acyl group. A great deal of satisfactory achievements in the synthesis and application of enamides has been made in recent years. Especially, tertiary enamides without N-H bond regarded as low reactivity of compounds in the past can act as excellent nucleophiles to react with electrophiles for the construction of various nitrous molecules.

Objective: This review focuses on recent advances on tertiary enamides in the synthetic strategies and applications including addition, coupling reaction, functionalization and electro- or photo-chemical reaction.

Conclusion: Tertiary enamides as electron-deficient nucleophiles display a satisfactory balance between stability and reactivity to offer multiple opportunities for the construction of various functionalized nitrogencontaining compounds. Further exploration of the reactive mechanisms involved tertiary enamides and the development of novel and efficient transformations to generate ever more complex building blocks starting from tertiary enamides are particularly worth pursuing.

Keywords: Tertiary enamide, nucleophilic reaction, addition, coupling reaction, functionalization, electro- or photochemical reaction.

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