Aldehyde-Selective Wacker Oxidation in
a Thiyl-Mediated Vinyl Group Transfer
Route to Daunosamine
Gregory K. Friestad,*Tao Jiang, andAlex K. Mathies
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242
gregory-friestad@uiowa.edu
Received December 13, 2006
Abstract:
Asymmetric dihydroxylation, thiyl radical mediated transfer of a silicon-tethered vinyl group to a hydrazone and an unconventional aldehyde-selective Wacker oxidation are sequenced for an efficient synthesis of methyl N-trifluoroacetyl-L-daunosaminide in 32% overall yield from
crotonaldehyde.
