Synthesis of a polymer-supported oxazolidine aldehyde for asymmetric chemistry |
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Authors: | Wills A Jonathan Krishnan-Ghosh Yamuna Balasubramanian Shankar |
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Institution: | University Chemistry Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom. |
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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. |
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