Organic Chemistry Portal

Abstracts

Search:

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: jantillausf.edu

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

DOI: 10.1021/ol501789c  (free Supporting Information)



see article for more reactions

Abstract

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.

see article for more examples



Key Words

1,3-Oxazolidines


ID: J54-Y2014