Journal
ORGANIC LETTERS
Volume 23, Issue 3, Pages 706-710Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03909
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Funding
- National Natural Science Foundation of China [21525207, 21772147, 22071186, 22071187]
- Natural Science Foundation of Hubei Province [2020CFA036]
- Natural Science Foundation of Jiangsu Province [SKB2019041078]
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The Ir-catalyzed asymmetric tandem allylation/iso-Pictet-Spengler cyclization reaction provides a direct and practical approach for accessing tetrahydro-gamma-carboline derivatives with multiple functional groups and stereogenic centers in good to high yields and excellent stereoselective control. The wide substrate generality, easily available substrates, and simple chiral catalytic system demonstrate the great potential practicality of this efficient protocol.
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-gamma-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.
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