Abstract
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.
基金项目
国家自然科学基金(82073997)
国家自然科学基金(22001024)
四川省科技厅项目(2021YFS0044)
四川省科技厅项目(2021YJ0402)
Innovation Team and Talents Cultivation Program of National Administration of Traditional Chinese Medicine(ZYYCXTD-D-202209)
Xinglin Scholar Research Promotion Project of Chengdu University of TCM()
NETL
NSTL
维普
万方数据