Enantioselective construction of substituted hydantoins via chiral phosphoric acid catalyzed annulation/Heyns rearrangement of aryl-substituted ureas with glyoxals

被引：4
|
作者：
Wang, Yong [1 ,2 ]
Li, Jingyuan [3 ]
Li, Yanyan [1 ,2 ]
Pi, Chao [1 ,2 ]
Wu, Yangjie [1 ,2 ]
Cui, Xiuling [1 ,2 ]
机构：
[1] Zhengzhou Univ, Henan Key Lab Chem Biol & Organ Chem, Key Lab Appl Chem Henan Univ, Green Catalysis Ctr, 75 Daxue Rd North, Zhengzhou 450052, Peoples R China
[2] Zhengzhou Univ, Coll Chem, 75 Daxue Rd North, Zhengzhou 450052, Peoples R China
[3] Shanghai Jiao Tong Univ, Schl Chem & Chem Engn, Shanghai 200240, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 22期
关键词：
DERIVATIVES;
D O I：
10.1039/d3qo01194a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, the de novo organocatalyzed enantioselective construction of hydantoins from simple urea and glyoxal is reported. A chiral phosphoric acid (CPA) catalyzed [3 + 2] heteroannulation/enantioselective Heyns rearrangement is proposed to be involved in this transformation. The Heyns rearrangement smoothly proceeded via a proton-transfer process involving an enol intermediate. The CPA served as a chiral proton-transfer shuttle to control the enantioselectivity.
引用
收藏
页码：5631 / 5636
页数：6
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