Stereoselective capture of N-acyliminium ions generated from a-hydroxy-N-acylcarbamides: direct synthesis of uracils from barbituric acids enabled by SmI2 reduction.
Stereoselective capture of N-acyliminium ions generated from a-hydroxy-N-acylcarbamides: direct synthesis of uracils from barbituric acids enabled by SmI2 reduction.
复制标题
立体选择性捕获由α-羟基-N-酰基脲产生的N-酰亚胺离子：通过SmI2还原从巴比妥酸直接合成尿嘧啶。
DOI：
10.1021/ol403340j
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发表时间：
2014
期刊：
影响因子：
5.2
通讯作者：
Szostak M
中科院分区：
文献类型：
--
作者：
Szostak M
刘易斯酸促进巴比妥酸衍生的α-氨基醇通过化学选择性Sm（II）介导的电子转移裂解，得到广泛的C6-取代的5，6-二氢尿嘧啶。该反应涉及直接从多功能巴比妥酸生成第一代N-酰基异氰尿酸离子，并具有良好的立体选择性。所述产物显示在通用过渡金属催化的反应中具有活性，从而为具有生物学意义的尿嘧啶衍生物提供模块化且高度实用的序列。
Lewis acid promoted cleavage of α-amino alcohols derived from barbituric acids via chemoselective Sm(II)-mediated electron transfer affords a wide range of C6-substituted 5,6-dihydrouracils. The reaction involves the first generation ofN-acyliminium ions directly from the versatile barbituric acids and proceeds with excellent stereoselectivity. The products are shown to be active in generic transition metal catalyzed reactions, thus providing a modular and highly practical sequence to the biologically significant uracil derivatives.