Highly efficient synthesis and stereoselective migration reactions of chiral five-membered aza-spiroindolenines: scope and mechanistic understanding

An Ir-catalyzed asymmetric synthesis of five-membered aza-spiroindolenines is achieved. Based on the detailed investigation of the reaction patterns of the aryl iminium migration, a one-pot asymmetric allylic dearomatization/migration sequence from racemic indole derivatives is realized, affording e...

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Published inChemical science (Cambridge) Vol. 7; no. 7; pp. 4453 - 4459
Main Authors Wu, Qing-Feng, Zheng, Chao, Zhuo, Chun-Xiang, You, Shu-Li
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Aromatic compounds
Asymmetry
Bearing
Chemistry
Chemistry, Multidisciplinary
Derivatives
Indoles
Migration
Physical Sciences
Science & Technology
Synthesis
Synthesis (chemistry)
TANDEM REACTIONS
ASYMMETRIC ALLYLIC DEAROMATIZATION
ARYLATIVE DEAROMATIZATION
PICTET-SPENGLER REACTION
ENANTIOSELECTIVE SYNTHESIS
SPIRO INTERMEDIATE
PALLADIUM-CATALYZED REACTIONS
2,3-DISUBSTITUTED INDOLES
ELECTROPHILIC SUBSTITUTION
3-SUBSTITUTED INDOLES
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Summary:An Ir-catalyzed asymmetric synthesis of five-membered aza-spiroindolenines is achieved. Based on the detailed investigation of the reaction patterns of the aryl iminium migration, a one-pot asymmetric allylic dearomatization/migration sequence from racemic indole derivatives is realized, affording enantioenriched Pictet-Spengler-type products bearing an additional allylic stereogenic center adjacent to the C3 position of the indole core.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:2041-6520
2041-6539
DOI:10.1039/c6sc00176a