Synthesis of a polymer-supported oxazolidine aldehyde for asymmetric chemistry.
An expedient synthesis of the polymer-supported aldehyde 3, as a Garner aldehyde equivalent, is described. Oxazolidine 3 may be obtained through preformation of aldehyde linker 4 in solution and loaded onto amine-terminating resin under peptide-coupling conditions, or alternatively via oxidation of polymer-bound alcohol 14. The integrity of the serine-derived stereocenter is maintained through all steps of the synthesis.
Wills
A Jonathan
AJ
University Chemistry Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom.
Krishnan-Ghosh
Yamuna
Y
Balasubramanian
Shankar
S