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Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and 1,3‑Oxazinanes via Hemiaminal Intermediates

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journal contribution
posted on 17.12.2015, 04:29 by Sri Krishna Nimmagadda, Zuhui Zhang, Jon C. Antilla
A highly efficient method for the enantioselective one-pot synthesis of 1,3-oxazolidines and 1,3-oxazinanes has been reported. The reaction proceeds via the formation of hemiaminal intermediates obtained by the enantioselective addition of respective alcohols to imines catalyzed by a chiral magnesium phosphate catalyst, followed by intramolecular cyclization under mildly basic conditions. A wide range of substrates have been converted to the respective chiral heterocyclic products in high yields and with excellent enantioselectivities using this one-pot procedure.