Synfacts 2007(12): 1314-1314  
DOI: 10.1055/s-2007-991336
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Chemo- and Regioselective Acylation of Monosaccharides

Contributor(s): Benjamin List, Michael Stadler
T. Kawabata*, W. Muramatsu, T. Nishio, T. Shibata, H. Schedel
Kyoto University, Japan
Further Information

Publication History

Publication Date:
22 November 2007 (online)


The presented organocatalyst allows for the regio- and chemoselective acylation of the equatorial hydroxy group at carbon C(4) of monosaccharides. This is especially remarkable since the substrates not only contain a primary ­hydroxyl group but also two other secondary alcohols. The catalyst of choice contains a DMAP-type subunit as the active center and two tryptophans as directing groups. It mediates the acylations with usually high yields and in often excellent regio­selectivities. Mechanistic studies and transition-state models to explain the observed selectivities have been included in the paper.