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N‐Heterocyclic Carbene‐Catalyzed Umpolung Formal [3+3] Cycloaddition of Enals with Isatogens: Access to Fused Indolin‐3‐ones with a Tetrasubstituted Carbon Stereocenter
Author(s) -
Xu Junyu,
Hu Shihe,
Lu Yingyan,
Dong Ying,
Tang Weifang,
Lu Tao,
Du Ding
Publication year - 2015
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.201401070
Subject(s) - stereocenter , umpolung , chemistry , indole test , carbene , catalysis , cycloaddition , combinatorial chemistry , carbon fibers , stereochemistry , organic chemistry , enantioselective synthesis , nucleophile , computer science , algorithm , composite number
Abstract A novel synthetic method to access fused indolin‐3‐ones with a tetrasubstituted carbon stereocenter has been developed via NHC‐catalyzed umpolung formal [3+3] cycloaddtion of enals with isatogens. This methodology could be also applied for the quick construction of the 6‐5‐5 tricyclic pyrrolo[1,2‐ a ]indole skeleton which is frequently found as a core structure of many indole alkaloids.