Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 4-5, Pages 685-693Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600559
Keywords
chiral building blocks; deracemization; N-protected alkyl carbonates of 5-hydroxy-3-piperidenes; N-protected 5-hydroxy-3-piperidenes
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The palladium-catalyzed deracemization of N-protected alkyl carbonates of 5-hydroxy-3-piperidenes by use of chiral phosphine ligands is described. A Trost ligand such as (R)-BPA was found to be a suitable chiral ligand for the deracemization, providing N-protected 5-hydroxy-3-piperidenes in good yields with good to high enantioselectivities. A plausible mechanism for the reaction is proposed.
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