N-alkylation of indole via ring-closing metathesis/isomerization/Mannich cascade under ruthenium/chiral phosphoric acid sequential catalysis

Yan-Chao Shi; Shou-Guo Wang; Qin Yin; Shu-Li You

doi:10.1039/C3QO00008G

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N-alkylation of indole via ring-closing metathesis/isomerization/Mannich cascade under ruthenium/chiral phosphoric acid sequential catalysis†

Yan-Chao Shi,^a Shou-Guo Wang,^a Qin Yin^a and Shu-Li You*^a

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* Corresponding authors

^a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
E-mail: slyou@sioc.ac.cn
Fax: (+86) 21-54925087

Abstract

A sequential catalysis by combining the Zhan-1B catalyst with chiral phosphoric acid has been utilized for N-alkylation of indole through a ring-closing metathesis/double bond isomerization/Mannich reaction cascade. Enantioenriched γ-lactams were synthesized in up to 92% yield and 95% ee.

This article is part of the themed collection: Celebrating 70 Years of Shanghai Institute of Organic Chemistry

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Article information

DOI: https://doi.org/10.1039/C3QO00008G
Article type: Research Article
Submitted: 08 Oct 2013
Accepted: 25 Oct 2013
First published: 23 Dec 2013

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Org. Chem. Front., 2014,1, 39-43

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N-alkylation of indole via ring-closing metathesis/isomerization/Mannich cascade under ruthenium/chiral phosphoric acid sequential catalysis

Y. Shi, S. Wang, Q. Yin and S. You, Org. Chem. Front., 2014, 1, 39 DOI: 10.1039/C3QO00008G

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Organic Chemistry Frontiers

N-alkylation of indole via ring-closing metathesis/isomerization/Mannich cascade under ruthenium/chiral phosphoric acid sequential catalysis†

Abstract

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N-alkylation of indole via ring-closing metathesis/isomerization/Mannich cascade under ruthenium/chiral phosphoric acid sequential catalysis

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