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A Flexible Route to Chiral 2-endo-Substituted 9-Oxabispidines and Their Application in the Enantioselective Oxidation of Secondary Alcohols.

  作者 Breuning, Matthias;Steiner, Melanie;Mehler, Christian;Paasche, Alexander;Hein, David;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2009年74-3;  页码  1407-1410  
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[摘要]A new and flexible route to enantiomerically pure bi- and tricyclic 9-oxabispidines I (R = Me, Et) and II has been developed with use of (1R,5S)-7-methyl-2-oxo-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxy lic acid tert-Bu ester (III) as the common late-stage intermediate. The 9-oxabispidines synthesized were evaluated as the chiral ligands in the Pd(II)-catalyzed oxidative kinetic resoln. of secondary alcs. giving good to excellent selectivity factors of up to 19.

 
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