Tetrahedron letters

A convenient and practical method for N-acylation of 2-oxazolidinone chiral auxiliaries with acids

M Prashad, HY Kim, D Har, O Repic, TJ Blacklock

Index: Prashad, Mahavir; Kim, Hong-Yong; Har, Denis; Repic, Oljan; Blacklock, Thomas J. Tetrahedron Letters, 1998 , vol. 39, # 51 p. 9369 - 9372

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Citation Number: 28

Abstract

To a mixture of 2-oxazolidinone chiral auxiliary (1 eq.), acid (2 eq.) in toluene (1.6 mL/ mmol) was added triethylamine (4 eq.). The mixture was heated to an internal temperature of 80 °C to obtain a solution. To the reaction mixture was added a solution of pivaloyl chloride (2 eq.) in toluene (0.2 mL / mmol) at a rate to maintain an internal temperature of 80 °C. The mixture was then heated to an internal temperature of 110 °C and stirred at this temperature for ...