Selective C-tert-Butoxycarbonylation Using Di-tert-butyl Dicarbonate for the Synthesis of Multifunctional Carbon Compounds

Abstract

The reaction of di-tert-butyl dicarbonate (Boc₂O) in the presence of the acylation catalyst 4-dimethylaminopyridine (DMAP) was examined with N-Boc or N-acyl cyanoglycinate. The couple Boc₂O/DMAP was found to act as an efficient agent for ­selective C-tert-butoxycarbonylation affording multifunctional carbon compounds.

Key words

acylation - carbanion - regioselectivity - protecting groups - amino acids

References and Notes

• 1a Wakselman M. In Encyclopedia of Reagents for Organic Synthesis   Vol. 3:  Paquette LA. John Wiley and Sons; New York: 1995.  p.1602 
• 1b Mohapatra DK. Synlett  2001,  1995 
• 2 Greene TW. Wuts PGM. Protective Groups in Organic Chemistry   3rd ed.:  John Wiley and Sons; New York: 1999.  p.518 
• 3a Knölker HJ. Braxmeier T. Schlechtingen G. Angew. Chem., Int. Ed. Engl.  1995,  34:  2497 
• 3b Knölker HJ. Braxmeier T. Schlechtingen G. Synlett  1996,  502 
• 3c Knölker HJ. Braxmeier T. Tetrahedron Lett.  1996,  37:  5861 
• 4 Basel Y. Hassener A. J. Org. Chem.  2000,  65:  6368 
• 5 Mohapatra DK. Datta A. Synlett  1996,  1129 
• 6 Mohapatra DK. Datta A. J. Org. Chem.  1999,  64:  6879 
• 7 Grehn L. Gunnarsson K. Ragnarsson U. J. Chem. Soc., Chem. Commun.  1985,  1317 
• 8 Grehn L. Ragnarsson U. Angew. Chem., Int. Ed. Engl.  1985,  24:  510 
• 9 Duguay G. Guémas JP. Meslin JC. Pradère JP. Reliquet F. Reliquet A. Tea-Gokou C. Quiniou H. Rabiller C. J. Heterocycl. Chem.  1980,  17:  767 
• 10 Hudhomme P. Duguay G. Tetrahedron  1990,  46:  5263 
• 11 Chehna M. Hudhomme P. Blanchard P. Duguay G. Sulfur Lett.  1994,  17:  317 
• 12 Grehn L. Gunnarsson K. Ragnarsson U. Acta Chem. Scand. Ser. B  1986,  40:  745 
• 13a Takeuchi Y. Rev. Heteroat. Chem.  1991,  4:  64 
• 13b Fujiwara T. Takeuchi Y. J. Fluorine Chem.  2005,  126:  941