Issue 17, 2018

trans-1,2-Diaminocyclohexane-based sulfonamides as effective hydrogen-bonding organocatalysts for asymmetric Michael–hemiacetalization reaction

Abstract

An easily attainable bifunctional monosulfonamide derivative of DACH was an effective catalyst for Michael addition–hemiacetalization reactions, providing products with ees exceeding 99% under optimized conditions. High enantioselectivities were achieved with just 0.2% mol catalyst loading. The sulfonamide outperformed analogous thiourea and squaramide-based organocatalysts.

Graphical abstract: trans-1,2-Diaminocyclohexane-based sulfonamides as effective hydrogen-bonding organocatalysts for asymmetric Michael–hemiacetalization reaction

Supplementary files

Article information

Article type
Paper
Submitted
08 Jun 2018
Accepted
27 Jul 2018
First published
31 Jul 2018

Catal. Sci. Technol., 2018,8, 4358-4363

trans-1,2-Diaminocyclohexane-based sulfonamides as effective hydrogen-bonding organocatalysts for asymmetric Michael–hemiacetalization reaction

M. Dajek, R. Kowalczyk and P. J. Boratyński, Catal. Sci. Technol., 2018, 8, 4358 DOI: 10.1039/C8CY01199K

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