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Synthesis 1996; 1996(11): 1283-1285
DOI: 10.1055/s-1996-4402
short paper
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Simple and Efficient N-Acylation Reactions of Chiral Oxazolidine Auxiliaries

David J. Ager* , David R. Allen1 , David R. Schaad1
  • *NSC Technologies, A unit of Monsanto, 601 E. Kensington Road, Mount Prospect, Illinois 60056, USA, Fax +1(847)5062200
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Publication Date:
31 December 2000 (online)

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A simplified procedure for the N-acylation of oxazolidin-2-one chiral auxiliaries has been developed. The acylations occur at room temperature in the presence of triethylamine and catalytic quantities of 4-(N,N-dimethylamino)pyridine, thereby eliminating the necessity for a strong base such as butyllithium. Acylations with both symmetrical and mixed anhydrides, as well as acid chlorides, occur with a wide variety of oxazolidinone auxiliaries.

oxazolidinones - N-acylation - chiral auxiliaries

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