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

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

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Abstract

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
Volume57
Issue number24
DOIs
StatePublished - Feb 24 2021
Externally publishedYes

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