Stereoselective Synthesis of β-Alkoxy-β-amido Vinylbenziodoxoles via Iodo(III)etherification of Ynamides
Stereoselective Synthesis of β-Alkoxy-β-amido Vinylbenziodoxoles via Iodo(III)etherification of Ynamides
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DOI：
10.1021/acs.orglett.2c02570
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发表时间：
2022-09-20
期刊：
影响因子：
5.2
通讯作者：
Yoshikai, Naohiko
中科院分区：
文献类型：
--
作者：
Kikuchi, Jun;Maesaki, Kaito;Yoshikai, Naohiko
报道了苯并碘、三氟化钠和醇的反式碘(III)醚化反应。尽管芳胺和烯胺对Bronsted酸很敏感，但该反应可以在严格控制的条件下成功地进行，以中等到较好的产率合成β-烷氧基-β-氨基-乙烯基苯并碘杂。产物可以通过C-I(III)键裂解和生成的α-烷氧基烯胺的亲电卤化反应进行一系列交叉偶联，从而制备出稠密官能化的酯。
A trans-iodo(III)etherification reaction of ynamides with benziodoxole triflate and alcohols is reported. Despite the sensitivity of ynamides and enamides toward Bronsted acid, the reaction could be successfully performed under carefully controlled conditions to afford beta-alkoxy-beta-amido vinylbenziodoxoles in moderate to good yields. The products could be subjected to a sequence of cross-coupling via C-I(III) bond cleavage and electrophilic halogenation of the resulting alpha-alkoxyenamides, allowing for the preparation of densely functionalized esters.