Asymmetric catalytic [4+3] cycloaddition ofortho-quinone methides with oxiranes

Qingfa Tan, Han Yu, Yao Luo, Fenzhen Chang, Xiaohua Liu, Yuqiao Zhou, Xiaoming Feng

Research output: Contribution to journalArticlepeer-review

22 Scopus citations


Catalytic enantioselective [4+3] cycloaddition reaction betweeno-quinone methides and oxiranes was achieved by using a chiralN,N′-dioxide/TbIIIcomplex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%) with good to excellent diastereo-(up to 94 : 6 dr) and enantioselectivities (up to 97% ee). The topographic steric maps and distribution of the buried volume (%VBur) of the catalystsviaCavallo's SambVca 2 tool were collected to effectively represent the chiral pocket of metal complexes of chiralN,N′-dioxides.
Original languageEnglish (US)
Pages (from-to)3018-3021
Number of pages4
JournalChemical Communications
Issue number24
StatePublished - Feb 24 2021
Externally publishedYes

Bibliographical note

KAUST Repository Item: Exported on 2022-06-15
Acknowledgements: We appreciate the National Natural Science Foundation of China (21890723, and 21625205) for financial support. The authors give thanks to Dr Luigi Cavallo (KAUST) and Dr Emanuel Hupf (Freie Universität Berlin) for the help in the application of the SambVca 2 suite.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.


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