对映选择合成
亲电胺化
胺化
化学
磷酸
组合化学
电泳剂
戒指(化学)
催化作用
有机化学
作者
Donglei Wang,Yuanhu Shao,Yunrong Chen,Xiao‐Song Xue,Xiaoyu Yang
标识
DOI:10.1002/anie.202201064
摘要
An efficient approach for asymmetric synthesis of planar-chiral macrocycles (paracyclophanes) has been disclosed through enantioselective electrophilic aromatic aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. A wide range of chiral macrocycles bearing varied ring sizes (16 to 23-membered) and functional group-containing ansa chains were readily afforded using this method, with excellent yields and high enantioselectivities (23 examples, up to 99.5 : 0.5 er). Experimental studies and DFT calculations were performed to elucidate the mechanism and origin of stereoselectivities of these reactions. Preliminary utilization of the planar-chiral macrocycle as chiral organocatalyst showcased the potential applications of these novel chiral skeletons.
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