Catalytic asymmetric synthesis of chiral thiohydantoins via the domino cyclization reaction of β,γ-unsaturated α-ketoesters and N,N′-dialkylthiourea

被引：2

作者：

Zhang, Meng-Cheng ^{[1
]}

Wang, Dong-Chao ^{[2
]}

Qu, Gui-Rong ^{[2
]}

Guo, Hai-Ming ^{[1
,2
]}

机构：

[1] Henan Normal Univ, Sch Environm, Xinxiang 453007, Henan, Peoples R China

[2] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Sch Chem & Chem Engn,Key Lab Green Chem Media & R, Minist Educ,NMPA Key Lab Res & Evaluat Innovat Dr, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 16期

关键词：

ANDROGEN RECEPTOR ANTAGONISTS; FORMAL 3+2 CYCLOADDITION; ENANTIOSELECTIVE CONSTRUCTION; BIOLOGICAL EVALUATION; CASCADE REACTION; SIMPLE OLEFINS; BICYCLIC N; O; KETO ESTERS; DERIVATIVES; ANTIANDROGEN;

D O I：

10.1039/d2qo00669c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic asymmetric route to synthesize chiral thiohydantoins containing a quaternary stereogenic center has been established using a chiral phosphoric acid catalyzed domino cyclization reaction of N,N '-dialkyl thioureas with beta,gamma-unsaturated alpha-ketoesters. By applying a chiral phosphoric acid catalyst, various chiral thiohydantoins containing a hemiaminal structure were obtained in high yields and excellent enantioselectivities (up to 97% ee) and two C-N bonds could be constructed in this reaction.

引用

页码：4358 / 4364

页数：7

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