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

Full Text: HTML

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 ...

Related Articles:

Carbon–carbon bond-forming reactions of α-carbonyl carbocations: exploration of a reversed-polarity equivalent of enolate chemistry

[Lai, Ping-Shan; Dubland, Joshua A.; Sarwar, Mohammed G.; Chudzinski, Michael G.; Taylor, Mark S. Tetrahedron, 2011 , vol. 67, # 39 p. 7586 - 7592]

Potent Kv1. 3 inhibitors from correolide—modification of the C18 position

[Bao, Jianming; Miao, Shouwu; Kayser, Frank; Kotliar, Andrew J.; Baker, Robert K.; Doss, George A.; Felix, John P.; Bugianesi, Randal M.; Slaughter, Robert S.; Kaczorowski, Gregory J.; Garcia, Maria L.; Ha, Sookhee N.; Castonguay, Laurie; Koo, Gloria C.; Shah, Kashmira; Springer, Marty S.; Staruch, Mary Jo; Parsons, William H.; Rupprecht, Kathleen M. Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 2 p. 447 - 451]

More Articles...