Relay Annulation of Ammonium Ylides with Oxindole-Derived α,β-Unsaturated Ketimines: Catalytic Construction of Spiro-polycyclic Oxindoles

An ammonium ylide-based relay annulation was disclosed, which uses DABCO as the catalyst and oxindole-derived α,β-unsaturated ketimines and γ-bromo-crotonates as the starting materials. This method enables the rapid assembly of a series of structurally novel spiro-polycyclic oxindoles containing a b...

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Published inOrganic letters Vol. 26; no. 24; pp. 5115 - 5119
Main Authors Zheng, Wei-Hao, Lv, Jing-Fang, He, Shi-Mei, Yu, Ning, Zhou, Yu-Qiang, Yang, Yun-Bo, Liu, Lv-Yan, He, Kui-Cheng, Wei, Ye, Jiang, Kun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.06.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANOCATALYTIC CYCLOPROPANATION
SPIROCYCLIC OXINDOLES
ACCESS
SPIROOXINDOLES
ENALS
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Summary:An ammonium ylide-based relay annulation was disclosed, which uses DABCO as the catalyst and oxindole-derived α,β-unsaturated ketimines and γ-bromo-crotonates as the starting materials. This method enables the rapid assembly of a series of structurally novel spiro-polycyclic oxindoles containing a bicyclo[4.1.0]­heptane moiety through simultaneous generation of three new bonds and two rings in one step under mild reaction conditions.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01442