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Regioselective Oxidative Cleavage of Benzylidene Acetals: Synthesis of α- and β-Benzoyloxy Carboxylic Acids


  • We thank DST and CSIR, India for financial support and DST-FIST for providing NMR facilities. P.S.K. and A.B. thank DST (Unit on Nano Science and Technology) and CSIR, New Delhi, for research fellowships. We thank V. Ram Kumar for single-crystal X-ray analysis.


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Ruthenium has twice the fun: The synthetic potential of the highly regio- and stereoselective title reaction, which relies on two oxidative cleavage steps promoted by RuCl3 in combination with NaIO4 (see example; Bz=benzoyl), was demonstrated with the synthesis of biologically active cis-(2R,3S)-3-hydroxypipecolic acid from D-glucose.

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