化学
催化作用
氧化还原
电子转移
环加成
光化学
有机化学
作者
Wenhui Wei,Chunyang Li,Yifan Fan,Xiaowei Chen,Xiaowei Zhao,Baokun Qiao,Zhiyong Jiang
标识
DOI:10.1002/anie.202406845
摘要
Abstract Consecutive photoinduced electron transfer (ConPET) is a powerful and atom‐economical protocol to overcome the limitations of the intrinsic redox potential of visible light‐absorbing photosensitizers, thereby considerably improving the substrate and reaction types. Likely because such an exothermic single‐electron transfer (SET) process usually does not require the aid of chiral catalysts, resulting in an inevitable racemic background reaction, notably, no enantioselective manifolds have been reported. Herein, we report on the viability of cooperative ConPET and chiral hydrogen‐bonding catalysis for the [3+2] photocycloaddition of cyclopropyl ketones with vinylazaarenes. In addition to enabling the first use of olefins that preferentially interact with chiral catalysts, this catalysis platform paves the way for the efficient synthesis of pharmaceutically and synthetically important cyclopentyl ketones functionalized by azaarenes with high yields, ees and dr. The robust capacity of the method can be further highlighted by the low loading of the chiral catalyst (1.0 mol %), the good compatibility of both 2‐azaarene and 3‐pyridine‐based olefins, and the successful concurrent construction of three stereocenters on cyclopentane rings involving an elusive but important all‐carbon quaternary.
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