Umpolung Reaction of α-Imino Thioesters and the Subsequent C-C Bond Formation with the Unexpected Alkylthio Rearrangement
Umpolung Reaction of α-Imino Thioesters and the Subsequent C-C Bond Formation with the Unexpected Alkylthio Rearrangement
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DOI：
10.1021/acs.orglett.8b00639
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发表时间：
2018-04-20
期刊：
影响因子：
5.2
通讯作者：
Shimizu, Makoto
中科院分区：
文献类型：
--
作者：
Mizota, Isao;Ueda, Chihiro;Shimizu, Makoto
我们检查了α-亚氨基硫酯的反极性反应，发现α-亚氨基硫酯是比传统α-亚氨基酯更有效的反极性N-烷基化底物，并且它们在温和的反应条件下在短时间内以高收率得到N-烷基化氨基硫酯。一种新型的C-C键形成，随后烷硫基与不饱和酮发生意想不到的重排，以高产率提供具有良好非对映选择性的β-烷硫基-α-氨基硫酯。
An umpolung reaction of the alpha-imino thioester was examined, and we found that alpha-imino thioesters were more effective substrates for the umpolung N-alkylation than conventional alpha-imino esters and they gave N-alkylated amino thioesters in high yields under mild reaction conditions in a short time. A new type of C-C bond formation followed by an unexpected rearrangement of the alkylthio group took place with the unsaturated ketones to afford the beta-alkylthio-alpha-amino thioesters in high yields with good diastereoselectivity.