Issue 18, 2013

Synergistic effects within a C2-symmetric organocatalyst: the potential formation of a chiral catalytic pocket

Abstract

This study describes the synthesis of five novel C2-symmetric organocatalysts that facilitate the on-water asymmetric aldol reaction at low catalyst loading (1 mol%) without the use of additives. Each catalyst is composed of two diprolinamide units joined by a symmetric alkyl bridging group allowing for systematic modulation of catalytic site proximity. Typically, catalysts in this manuscript which bear the catalytic units in close proximity gave the best reaction outcomes in terms of conversion (up to >99%), diastereomeric ratio (4/96, syn/anti) and enantiomeric excess (up to 97%). This effect has been attributed to the assembly of a chiral pocket, facilitated by hydrogen bonding at the oil-in-water interface.

Graphical abstract: Synergistic effects within a C2-symmetric organocatalyst: the potential formation of a chiral catalytic pocket

Supplementary files

Article information

Article type
Paper
Submitted
20 Nov 2012
Accepted
15 Feb 2013
First published
18 Feb 2013
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2013,11, 2951-2960

Synergistic effects within a C2-symmetric organocatalyst: the potential formation of a chiral catalytic pocket

J. P. Delaney, H. L. Brozinski and L. C. Henderson, Org. Biomol. Chem., 2013, 11, 2951 DOI: 10.1039/C3OB27250H

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