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

Sri Krishna Nimmagadda, Zuhui Zhang and Jon C. Antilla*

*Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, CHE205A, Tampa, Florida 33620, United States, Email:

S. K. Nimmagadda, Z. Zhang, J. C. Antilla, Org. Lett., 2014, 16, 4098-4101.

DOI: 10.1021/ol501789c

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A highly efficient one-pot synthesis of a wide range of 1,3-oxazolidines and 1,3-oxazinanes in high yields and with excellent enantioselectivities proceeds in the presence of a chiral magnesium phosphate catalyst via the formation of hemiaminal intermediates obtained by the enantioselective addition of respective alcohols to imines followed by intramolecular cyclization under mildly basic conditions.

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ID: J54-Y2014