Organocatalytic regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives: suppression of cycloolefin isomerisation by employing sterically demanding catalysts

Hui Mao; Dong Wan Kim; Hun Yi Shin; Choong Eui Song; Jung Woon Yang

doi:10.1039/C6OB01918H

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Organocatalytic regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives: suppression of cycloolefin isomerisation by employing sterically demanding catalysts†

Hui Mao,

‡^a Dong Wan Kim,‡^a Hun Yi Shin,‡^a Choong Eui Song

*^b and Jung Woon Yang

*^a

Author affiliations

* Corresponding authors

^a Department of Energy Science, Sungkyunkwan University, 2066 Seobu-ro, Jangan-gu, Suwon, Gyeonggi-do 16419, South Korea
E-mail: jwyang@skku.edu
Tel: +82-31-299-4276

^b Department of Chemistry, Sungkyunkwan University, 2066 Seobu-ro, Jangan-gu, Suwon, Gyeonggi-do 16419, South Korea
E-mail: s1673@skku.edu

Abstract

The regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives was achieved through transition-metal-free, reductive cyclisation of ortho-formyl trans-cinnamaldehydes with Hantzsch ester in the presence of an aminocatalyst. In particular, cycloolefin isomerisation of the resulting products could be inhibited efficiently by the introduction of a sterically demanding stereo-defined aminocatalyst.

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Article information

DOI: https://doi.org/10.1039/C6OB01918H
Article type: Paper
Submitted: 31 Aug 2016
Accepted: 08 Nov 2016
First published: 08 Nov 2016

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Org. Biomol. Chem., 2017,15, 1355-1362

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Organocatalytic regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives: suppression of cycloolefin isomerisation by employing sterically demanding catalysts

H. Mao, D. W. Kim, H. Y. Shin, C. E. Song and J. W. Yang, Org. Biomol. Chem., 2017, 15, 1355 DOI: 10.1039/C6OB01918H

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Organic & Biomolecular Chemistry

Organocatalytic regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives: suppression of cycloolefin isomerisation by employing sterically demanding catalysts†

Abstract

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Organocatalytic regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives: suppression of cycloolefin isomerisation by employing sterically demanding catalysts

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