Synthesis of isolable β-chloroenamines from N-alkoxylactams with organometallic reagents
Synthesis of isolable β-chloroenamines from N-alkoxylactams with organometallic reagents
复制标题
用有机金属试剂从 N-烷氧基内酰胺合成可分离的 β-氯烯胺
DOI：
10.1039/d2ob02151j
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发表时间：
2023
期刊：
影响因子：
--
通讯作者：
Ueda Masafumi
中科院分区：
文献类型：
--
作者：
Takeda Norihiko;Suganuma Riku;Yasui Motohiro;Ueda Masafumi
报道了一种通过α-氯代N-烷内酰胺与有机锂和Grignard试剂的亲核加成/脱水得到可分离的β-氯代烯胺的有效方法。这种方法适合于通过掺入各种C（sp）和C（sp2）单元，例如炔、芳基和杂芳基部分来合成β-氯烯胺。该顺序反应具有广泛的底物范围，并且可以进行用于可规模化合成β-氯烯胺。对比实验表明，氯和烷氧基作为诱导吸电子取代基，以提高稳定性的烯胺。
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.