Synthesis of a polymer-supported oxazolidine aldehyde for asymmetric chemistry.

Abstract:

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.

Authors:

AJ Wills, Y Krishnan-Ghosh, S Balasubramanian

Journal:

J Org Chem

Citation info:

67(19):6646-6652

Publication date:

20th Sep 2002

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