Remote stereocontrol in the(4+2)cycloadditions of 1,7-zwitterions:Asymmetric synthesis of multifunctionalized tetrahydroquinoline derivatives

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外文摘要：The scope of stereochemistry recognition usually occurs near the chiral scaffold of a ligand or catalyst.Remote stereocontrol,which can surpass the limits of stereorecognition of remote prochiral centers,has long been a challenging object of great interest in asymmetric catalysis.The current work realized the remote stereocontrol of 1,7-zwitterion intermediates formed from Huang's o-amino aryl MBH carbonates.With simple and easily accessible β-ICD as the bifunctional catalyst,multifunctionalized tetrahydroquino-line derivatives could be synthesized via(4+2)cycloadditions with excellent enantioselectivity and di-astereoselectivity under mild conditions.The strategy possesses broad substrate scope,and three types of electron-deficient enones are successfully applied.Mechanistic studies disclosed the Lewis base-catalyzed reaction pathway,and H-bonding between the catalyst and enones is crucial for long-range stereocontrol.Scale-up reaction and transformations of the tetrahydroquinoline products demonstrated the potential of this strategy.

外文关键词：

Asymmetric synthesisTetrahydroquinolineRemote stereocontrolPyrazoloneLewis base catalysis1,7-Zwitterion

作者：

Chen Chen、Jin Zhou、Jing Jiang、Yang Li、Ting Mao、Cheng Peng、Gu Zhan、Wei Huang

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作者单位：

State Key Laboratory of Southwestern Chinese Medicine Resources,School of Pharmacy,Chengdu University of Traditional Chinese Medicine,Chengdu 611137,China

基金：

国家自然科学基金国家自然科学基金四川省科技厅项目四川省科技厅项目Innovation Team and Talents Cultivation Program of National Administration of Traditional Chinese MedicineXinglin Scholar Research Promotion Project of Chengdu University of TCM

项目编号：

82073997220010242021YFS00442021YJ0402ZYYCXTD-D-202209

出版年：

2024

DOI：

10.1016/j.cclet.2023.108295

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCD

影响因子：0.771

ISSN：1001-8417

年,卷(期)：2024.35(1)

参考文献量87