947682-10-2Relevant academic research and scientific papers
Chiral 2-endo-substituted 9-oxabispidines: Novel ligands for enantioselective copper(ii)-catalyzed henry reactions
Breuning, Matthias,Hein, David,Steiner, Melanie,Gessner, Viktoria H.,Strohmann, Carsten
supporting information; experimental part, p. 12764 - 12769 (2010/06/14)
A flexible approach, applicable on a gram scale, to chiral 2-endosubstituted 9-oxabispidines was developed. The key intermediate, a cis-configured 6-aminomethylmorpholine-2carbonitrile, was prepared from (R)-3aminopropane-1,2-diol and 2-chloroacrylonitril
A flexible route to chiral 2-endo-substituted 9-oxabispidines and their application in the enantioselective oxidation of secondary alcohols
Breuning, Matthias,Steiner, Melanie,Mehler, Christian,Paasche, Alexander,Hein, David
supporting information; experimental part, p. 1407 - 1410 (2009/07/11)
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[33.1]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.
Enantioselective synthesis of 2-phenyl-9-oxabispidines
Breuning, Matthias,Steiner, Melanie
, p. 1702 - 1706 (2008/02/07)
A small selection of enantiomerically pure 2-phenyl-9-oxabispidines was synthesized in a three to five step procedure from commercially available starting materials. Ring opening of (R,R)-3-phenylglycidol with benzylamine, condensation with (S)-epichloroh
