Ir-Catalyzed Asymmetric Tandem Allylation/Iso-Pictet–Spengler Cyclization Reaction for the Enantioselective Construction of Tetrahydro-γ-carbolines

Ir-catalyzed asymmetric tandem allylation/iso-Pictet–Spengler cyclization of arylidenaminomalonates with indolyl allylic methyl carbonates was successfully developed, which provided a direct and practical approach to access synthetically useful and biologically active tetrahydro-γ-carboline derivati...

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Bibliographic Details
Published in:Organic letters 2021-02, Vol.23 (3), p.706-710
Main Authors: Xiao, Fan, Xu, Shi-Ming, Dong, Xiu-Qin, Wang, Chun-Jiang
Format: Article
Language:English
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Summary:Ir-catalyzed asymmetric tandem allylation/iso-Pictet–Spengler cyclization of arylidenaminomalonates with indolyl allylic methyl carbonates was successfully developed, which provided a direct and practical approach to access synthetically useful and biologically active tetrahydro-γ-carboline derivatives bearing multiple functional groups and stereogenic centers in good to high yields and excellent stereoselective control (44%–96% yields, >20:1 dr, 94% → 99% ee). A wide range of substrate generality, easily available substrates, and simple chiral catalytic system displayed great potential practicality of this efficient protocol.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03909