A flexible route to chiral 2-endo-substituted 9-oxabispidines and their application in the enantioselective oxidation of secondary alcohols.
A new and flexible route to enantiomerically pure bi- and tricyclic 9-oxabispidines has been developed with use of (1R,5S)-7-methyl-2-oxo-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester as the common late-stage intermediate. The 9-oxabispidines synthesized were evaluated as the chiral ligands in the Pd(II)-catalyzed oxidative kinetic resolution of secondary alcohols giving good to excellent selectivity factors of up to 19.
Breuning
Matthias
M
Institute of Organic Chemistry, University of Wurzburg, Am Hubland, 97074 Wurzburg, Germany. breuning@chemie.uni-wuerzburg.de
Steiner
Melanie
M
Mehler
Christian
C
Paasche
Alexander
A
Hein
David
D