Enantiopure 1,5-diols from dynamic kinetic asymmetric transformation: Useful synthetic intermediates for the preparation of chiral heterocycles

ORGN 593

Karin Leijondahl, karinl@organ.su.se, Linnéa Borén, Roland Braun, and Jan E. Bäckvall, jeb@organ.su.se. Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, SE-106 91 Stockholm, Sweden
Enantiomerically pure 1,5-diols are important synthetic intermediates for the preparation of 2,6-disubstituted six-membered heterocycles. Many of these are structural elements of natural products and biologically active compounds, and some can be used as chiral ligands.

Our group has developed a combined enzyme- and ruthenium-catalyzed dynamic kinetic resolution (DKR) which provides enantiopure acetates from racemic sec-alcohols. Recently, this protocol was applied to 1,3- and 1,4-diols, and the diacetates were obtained in excellent yield, enantioselectivity, and diastereoselectivity. In the present work a dynamic kinetic asymmetric transformation (DYKAT) of 1,5-diols afforded enantiopure diacetates. These chiral 1,5-diol derivatives can be easily transformed to a variety of 2,6-disubstituted six-membered heterocycles.

 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008