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Updated: Aug 14, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Synthesis of isolable β-chloroenamines from N-alkoxylactams with organometallic reagents
Norihiko Takeda1, Riku Suganuma1, Motohiro Yasui1
1Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan. masa-u@kobepharma-u.ac.jp.
Abstract:
An efficient approach to access isolable β-chloroenamines via nucleophilic addition/dehydration of α-chloro N-alkoxylactam with organolithium and Grignard reagents is reported. This approach is amenable to the synthesis of β-chloroenamines by incorporating various C(sp) and C(sp2) units, such as alkyne, aryl, and heteroaryl moieties. The sequential reaction has a broad substrate scope and can be carried out for a scalable synthesis of β-chloroenamines. Control experiments suggested that both chloro and alkoxy groups act as inductive electron-withdrawing substituents to improve the stability of the enamines.
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