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NHC‐Catalyzed Enantioselective [4+3] Cycloaddition of Ortho ‐Hydroxyphenyl Substituted Para ‐Quinone Methides with Isatin‐Derived Enals
Author(s) -
Li Wenjun,
Yuan Huijun,
Liu Zhantao,
Zhang Zhongyin,
Cheng Yuyu,
Li Pengfei
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800337
Subject(s) - enantioselective synthesis , chemistry , isatin , synthon , cycloaddition , annulation , oxindole , organocatalysis , moiety , catalysis , quinone , combinatorial chemistry , stereochemistry , organic chemistry
The first enantioselective cycloaddition of ortho ‐hydroxyphenyl substituted para ‐quinone methides has been established by employing isatin‐derived enals as suitable 3C‐synthons under chiral N ‐heterocyclic carbene catalysis. By using this strategy, biologically important ϵ‐lactones have been prepared in good yields (up to 89%) and excellent asymmetric inductions (up to >99% ee, >20:1 dr). Notably, this methodology opens a direct [4+3] annulation entry for the asymmetric synthesis of spirobenzoxopinones bearing an oxindole moiety connected through the spirocenter.