Synthesis 2006(14): 2297-2300  
DOI: 10.1055/s-2006-942455
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Enantiomerically Pure Diols and Diketones from Norbornadiene

Chong-lin Cai, Chun-Gu Xia*
State Key Laboratory of Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, and Graduate School of the Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
Fax: +86(931)8277088; e-Mail: cgxia@ns.lzb.ac.cn;
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Publikationsverlauf

Received 9 December 2005
Publikationsdatum:
28. Juni 2006 (online)

Abstract

The preparation of (1R,4R)-bicyclo[2,2,1]heptane-2,5-dione from norbornadiene with >99% ee is described. This compound was used to make the synthetically useful (1R,2R,4R,5R)-exo,exo-2,5-diphenylbicyclo[2,2,1]heptane-endo,endo-2,5-diol and (1R,2R,4R,5R)-endo,endo-bicyclo[2,2,1]heptane-2,5-diol, which may prove to be valuable building blocks for novel ligand synthesis.