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

页码：5631 / 5636

页数：6

共 50 条

[41] Chiral squaramides catalyzed diastereo-and enantioselective Michael addition of α-substituted isocyanoacetates to N-aryl maleimides
Zhao, Mei-Xin
Ji, Fei-Hu
Wei, Deng-Ke
Shi, Min
TETRAHEDRON, 2013, 69 (50) : 10763 - 10771
[42] Indium triflate catalyzed rearrangement of aryl-substituted cyclopropyl carbinols to 1,4-disubstituted 1,3-butadienes
Ranu, Brindaban C.
Banerjee, Subhash
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (13) : 3012 - 3015
[43] Europium-Catalyzed Intramolecular Addition of Carboxylic Acid to Nonactivated Alkenes: An Efficient Route to Aryl-Substituted γ-Butyrolactone
Bandyopadhyay, Manas
Nayak, Abhijit
Bera, Mrinal K.
SYNLETT, 2020, 31 (15) : 1474 - 1478
[44] Palladium-catalyzed ligand-free and aqueous Suzuki reaction for the construction of (hetero)aryl-substituted triphenylamine derivatives
Liu, Chun
Rao, Xiaofeng
Song, Xinlong
Qiu, Jieshan
Jin, Zilin
RSC ADVANCES, 2013, 3 (02): : 526 - 531
[45] SYNTHESIS OF ARYL-SUBSTITUTED ALDEHYDES AND KETONES VIA PALLADIUM-CATALYZED COUPLING OF ARYL HALIDES AND NON-ALLYLIC UNSATURATED ALCOHOLS
LAROCK, RC
LEUNG, WY
STOLZDUNN, S
TETRAHEDRON LETTERS, 1989, 30 (48) : 6629 - 6632
[46] Enantioselective synthesis of hetero-triarylmethanes by chiral phosphoric acid-catalyzed 1,4-addition of 3-substituted indoles with azadienes
Lu, Zhen-yu
Hu, Jin-tao
Lan, Wei-qiao
Mo, Xiao-qing
Zhou, Shuang
Tang, Yue-fan
Yuan, Wei-cheng
Zhang, Xiao-mei
Liao, Li-hua
TETRAHEDRON LETTERS, 2021, 67
[47] Enantioselective high-performance liquid chromatography of aryl-substituted oxazolines as an efficient tool for determination of chiral purity of serine medicinal components
Pomeisl, Karel
Vankatova, Petra
Hamplova, Vera
JOURNAL OF SEPARATION SCIENCE, 2022, 45 (13) : 2217 - 2227
[48] Chiral Phosphoric Acid Catalyzed Highly Enantioselective Friedel-Crafts Alkylation Reaction of C3-Substituted Indoles to β,γ-Unsaturated α-Ketimino Esters
Bi, Bo
Lou, Qin-Xin
Ding, Yu-Yang
Chen, Sheng-Wei
Zhang, Sha-Sha
Hu, Wen-Hui
Zhao, Jun-Ling
ORGANIC LETTERS, 2015, 17 (03) : 540 - 543
[49] Synthesis of aryl-substituted quinoline derivatives via Bronsted acid-catalyzed [4+2] aza Diels-Alder reaction
Akiyama, T
Nakashima, S
Yokota, K
Fuchibe, K
CHEMISTRY LETTERS, 2004, 33 (07) : 922 - 923
[50] Atroposelective Construction of Naphthylpyrazoles by Chiral Phosphoric Acid Catalyzed Enantioselective Cross-Coupling of Pyrazoles with Naphthoquinone Esters
Luo, Xi
Li, Sen
Tian, Yuting
Tian, Yuqi
Gao, Limei
Wang, Qiang
Zheng, Yongsheng
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (23)

← 1 2 3 4 5 →