Enantioselective Dearomative Arylation of Isoquinolines

The C1-substituted tetrahydroisoquinolines and 1,2-dihydroisoquinoline constitute an important group and are interesting structural motifs found in many natural products and pharmaceuticals. In this context, a phosphoric-acid-catalyzed enantioselective dearomative arylation of isoquinolines was real...

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Bibliographic Details
Published inACS catalysis Vol. 6; no. 8; pp. 5290 - 5294
Main Authors Zhang, Ming, Sun, Wangsheng, Zhu, Gongming, Bao, Guangjun, Zhang, Bangzhi, Hong, Liang, Li, Min, Wang, Rui
Format Journal Article
LanguageEnglish
Published American Chemical Society 05.08.2016
Subjects
isoquinolines
indole
chiral phosphoric acid
dearomative arylation
enantioselective
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Summary:The C1-substituted tetrahydroisoquinolines and 1,2-dihydroisoquinoline constitute an important group and are interesting structural motifs found in many natural products and pharmaceuticals. In this context, a phosphoric-acid-catalyzed enantioselective dearomative arylation of isoquinolines was realized, providing the chiral dihydroisoquinolines with indole substituents at the C1-position in good results (up to >99% yield and 97% ee). The reaction features mild reaction conditions and operational simplicity, which make it an attractive approach to the discovery of biologically interesting α-indolisoquinolines.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.6b01693