132836-68-1Relevant articles and documents
Substrate Acidities and Conversion Times for Reactions of Amides With Di-tert-butyl Dicarbonate
Hansen, Marvin M.,Harkness, Allen R.,Coffey, D. Scott,Bordwell, Frederick G.,Zhao, Yongyu
, p. 8949 - 8952 (1995)
The conversion time for 4-dimethylaminopyridine catalyzed reaction of amides with tert-butyl dicarbonate varies dramatically with substrate acidity.The pKa's in DMSO of some amides are determined to support correlation of reactivity with substr
Simple and efficient N-acylation reactions of chiral oxazolidinone auxiliaries
Ager, David J.,Allen, David R.,Schaad, David R.
, p. 1283 - 1285 (2007/10/03)
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.