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A flexible route to chiral 2-endo-substituted 9-oxabispidines and their application in the enantioselective oxidation of secondary alcohols.

作者信息

Breuning Matthias, Steiner Melanie, Mehler Christian, Paasche Alexander, Hein David

机构信息

Institute of Organic Chemistry, University of Wurzburg, Am Hubland, 97074 Wurzburg, Germany.

出版信息

J Org Chem. 2009 Feb 6;74(3):1407-10. doi: 10.1021/jo802409x.

DOI:10.1021/jo802409x
PMID:19086891
Abstract

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.

摘要

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