Issue 4, 2018

The cinchona alkaloid squaramide catalyzed asymmetric Pictet–Spengler reaction and related theoretical studies

Abstract

The asymmetric Pictet–Spengler reaction between tryptamine derivatives and aldehydes has been developed with a cinchona alkaloid squaramide as the catalyst, affording the corresponding tetrahedron-β-carbolines in good to excellent yields and ee values. A rational mechanistic pathway has also been proposed based on DFT calculations.

Graphical abstract: The cinchona alkaloid squaramide catalyzed asymmetric Pictet–Spengler reaction and related theoretical studies

Supplementary files

Article information

Article type
Paper
Submitted
24 Oct 2017
Accepted
15 Dec 2017
First published
15 Dec 2017

Org. Biomol. Chem., 2018,16, 566-574

The cinchona alkaloid squaramide catalyzed asymmetric Pictet–Spengler reaction and related theoretical studies

L. Qi, H. Hou, F. Ling and W. Zhong, Org. Biomol. Chem., 2018, 16, 566 DOI: 10.1039/C7OB02606D

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