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Updated: Apr 23, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
One-pot synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a
Juan Yao1, Lanxiang Zhou, Chen Tan
1School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou, 225002, Jiangsu, People's Republic of China.
Abstract:
An effective and practical method has been developed for the diversity-oriented synthesis of fully substituted cyclohexene β-aminoester via a pseudo five-component reaction between nitromethane, aromatic aldehydes, and substituted cyanoacetate for the generation of a wide range of structurally relevant and highly functionalized compounds. The attractive range and features of the method, which enables the facile preparation of highly substituted cyclohexenes, are its simple and straightforward procedure, mild reaction conditions, and ideal yields. The mechanism involves a double Michael addition reaction followed by intramolecular ring closure. The fully substituted cyclohexene β-aminoesters with potential bioactivities could be of impact in medical chemistry.
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Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...