Organocatalytic Enantioselective Protonation for Photoreduction of Activated Ketones and Ketimines Induced by Visible Light
Organocatalytic Enantioselective Protonation for Photoreduction of Activated Ketones and Ketimines Induced by Visible Light
复制标题
可见光诱导的活化酮和酮亚胺光还原的有机催化对映选择性质子化
DOI：
10.1002/anie.201707899
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发表时间：
2017-10-23
影响因子：
16.6
通讯作者：
Jiang, Zhiyong
中科院分区：
文献类型：
--
作者：
Lin, Lu;Bai, Xiangbin;Jiang, Zhiyong
首次报道了1，2-二酮和α-酮基酮亚胺在可见光照射下的催化不对称光还原反应。利用二氰基吡嗪衍生的发色团（DPZ）作为光氧化还原催化剂和非共价手性有机催化剂的无过渡金属协同催化平台对这些转化是有效的。通过在H+转移交换中灵活地使用手性Bronsted酸或碱来控制难以实现的对映选择性质子化，以高产率和对映选择性合成了多种手性α-羟基酮和α-氨基酮。
The first catalytic asymmetric photoreduction of 1,2-diketones and alpha-keto ketimines under visible light irradiation is reported. A transition-metal-free synergistic catalysis platform harnessing dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst and a non-covalent chiral organocatalyst is effective for these transformations. With the flexible use of a chiral Bronsted acid or base in H+ transfer interchange to control the elusive enantioselective protonation, a variety of chiral alpha-hydroxy ketones and alpha-amino ketones were obtained with high yields and enantioselectivities.