4.6 Article

Intramolecular hydrogen bonding guides a cationic amphiphilic organocatalyst to highly stereoselective aldol reactions in water

Journal

RSC ADVANCES
Volume 5, Issue 77, Pages 62331-62335

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ra12135c

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Funding

  1. Ministerio de Economia y Competitividad [CTQ2012-38594-C02-02, CTQ2012-38543-C0303]
  2. Generalitat de Catalunya [2014 SGR 231]

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A novel amphiphilic guanidine organocatalyst, efficient for asymmetric aldol reactions of ketones in water at neutral pH, is disclosed. The reaction presented a clear substrate dependence depicting a free energy linear correlation with ee. Intramolecular hydrogen bonding in the acylguanidine moiety was identified as the key structural motif.

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