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Issue 81, 2014
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Organocatalytic enantioselective and (Z)-selective allylation of 3-indolylmethanol via hydrogen-bond activation

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Abstract

An organocatalytic asymmetric allylation of 3-indolylmethanol has been established via hydrogen-bond activating mode, which directly assembles isatin-derived 3-indolylmethanols and o-hydroxystyrenes into chiral allyl-substituted oxindoles with one all-carbon quaternary stereogenic center and one newly formed C[double bond, length as m-dash]C bond in excellent enantioselectivity and (Z)-selectivity (up to 97% ee, >20 : 1 Z/E ratio). This transformation provides an efficient strategy for asymmetric C3-functionalization of indoles and allylation of 3-indolylmethanols with precise control of the stereoselectivity in the formation of C–C and C[double bond, length as m-dash]C bonds.

Graphical abstract: Organocatalytic enantioselective and (Z)-selective allylation of 3-indolylmethanol via hydrogen-bond activation

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Article information


Submitted
19 Mar 2014
Accepted
19 May 2014
First published
22 May 2014

Chem. Commun., 2014,50, 12054-12057
Article type
Communication

Organocatalytic enantioselective and (Z)-selective allylation of 3-indolylmethanol via hydrogen-bond activation

Y. Liu, H. Zhang, Y. Zhang, Y. Jiang, F. Shi and S. Tu, Chem. Commun., 2014, 50, 12054
DOI: 10.1039/C4CC02056A

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