Organocatalytic and enantioselective [4+2] cyclization between hydroxymaleimides and ortho -hydroxyphenyl para -quinone methide-selective preparation of chiral hemiketals

A cinchona alkaloid squaramide promoted enantioselective [4+2] cyclization between hydroxymaleimides and ortho -hydroxyphenyl p -QMs has been disclosed, and a wide range of chiral hemiketals containing chromane and succinimide frameworks with two adjacent quaternary stereogenic centers have been pre...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2020-12, Vol.56 (94), p.14825-14828
Hauptverfasser: Xiang, Min, Li, Chen-Yi, Song, Xiang-Jia, Zou, Ying, Huang, Zhi-Cheng, Li, Xia, Tian, Fang, Wang, Li-Xin
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Sprache:eng
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Zusammenfassung:A cinchona alkaloid squaramide promoted enantioselective [4+2] cyclization between hydroxymaleimides and ortho -hydroxyphenyl p -QMs has been disclosed, and a wide range of chiral hemiketals containing chromane and succinimide frameworks with two adjacent quaternary stereogenic centers have been prepared for the first time with excellent results (up to 99% yield, up to 99 : 1 dr, up to >99% ee) under mild conditions.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc06777f