Enantioselective Synthesis of Cyclobutane Derivatives via Cascade Asymmetric Allylic Etherification/[2+2] Photocycloaddition

被引:19
作者
Yang, Pusu [1 ]
Wang, Rui-Xiang [1 ]
Huang, Xu-Lun [1 ]
Cheng, Yuan-Zheng [1 ]
You, Shu-Li [1 ]
机构
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, New Cornerstone Sci Lab,State Key Lab Organometal, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
PHOTOCATALYSIS; ISOMERIZATION; ALKYLATION; CYCLOADDITION; CONSTRUCTION; ALLYLATION; STATE;
D O I
10.1021/jacs.3c08792
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral cyclobutane presents as a popular motif in natural products and biologically active molecules, and its derivatives have been extensively used as key synthons in organic synthesis. Herein, we report an efficient synthetic method toward enantioenriched cyclobutane derivatives. The reaction proceeds in a cascade fashion involving Ir-catalyzed asymmetric allylic etherification and visible-light induced [2 + 2] cycloaddition. Readily available branched allyl acetates and cinnamyl alcohols are directly used as the substrates under mild reaction conditions, providing a broad range of chiral cyclobutanes in good yields with excellent diastereo- and enantioselectivities (up to 12:1 dr, >99% ee). It is worth noting that all substrates and catalysts were simultaneously added without any separated step in this approach. The gram-scale reaction and diverse transformations of product further enhance the potential utility of this method.
引用
收藏
页码:21752 / 21759
页数:8
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