μ-Oxo-Dinuclear-Iron(III)-Catalyzed O-Selective Acylation of Aliphatic and Aromatic Amino Alcohols and Transesterification of Tertiary Alcohols

Rikiya Horikawa; Chika Fujimoto; Ryo Yazaki; Takashi Ohshima

doi:10.1002/chem.201602801

μ-Oxo-Dinuclear-Iron(III)-Catalyzed O-Selective Acylation of Aliphatic and Aromatic Amino Alcohols and Transesterification of Tertiary Alcohols

Chemistry. 2016 Aug 22;22(35):12278-81. doi: 10.1002/chem.201602801. Epub 2016 Jul 28.

Authors

Rikiya Horikawa¹, Chika Fujimoto¹, Ryo Yazaki¹, Takashi Ohshima²

Affiliations

¹ Graduate school of Pharmaceutical Sciences, Kyushu University, Maidashi Higashi-ku, Fukuoka, 812-8582, Japan.
² Graduate school of Pharmaceutical Sciences, Kyushu University, Maidashi Higashi-ku, Fukuoka, 812-8582, Japan. ohshima@phar.kyushu-u.ac.jp.

PMID: 27309126
DOI: 10.1002/chem.201602801

Abstract

A highly chemoselective and reactive μ-oxo-dinuclear iron(III) salen catalyst for transesterification was developed. The developed iron complex catalyzed acylation of aliphatic amino alcohols with nearly perfect O-selectivity, even when using activated esters, for which chemoselectivity is more difficult to control. In addition, O-selective transesterification of aromatic amino alcohols was achieved for the first time. The high activity of the iron complex enabled the use of sterically congested tertiary alcohols, including unprecedented tert-butanol.

Keywords: alcohols; chemoselectivity; iron; tert-butyl ester; transesterification.