41890-58-8Relevant articles and documents
Boc-protected amines via a mild and efficient one-pot curtius rearrangement
Lebel, Helene,Leogane, Olivier
, p. 4107 - 4110 (2005)
(Chemical Equation Presented) The reaction of a carboxylic acid with di-tert-butyl dicarbonate and sodium azide allowed the formation of an acyl azide intermediate, which undergoes a Curtius rearrangement in the presence of tetrabutylammonium bromide and zinc(II) triflate. The trapping of the isocyanate derivative in the reaction mixture led to the desired tert-butyl carbamate in high yields at low temperature. These reaction conditions are compatible with a variety of substrates, including malonate derivatives, which provide access to protected amino acids.
Catalytic enantioselective construction of all-carbon quaternary stereocenters: Synthetic and mechanistic studies of the C-acylation of silyl ketene acetals
Mermerian, Ara H.,Fu, Gregory C.
, p. 5604 - 5607 (2007/10/03)
With the aid of an appropriate chiral catalyst, acyclic silyl ketene acetals react with anhydrides to furnish 1,3-dicarbonyl compounds that bear all-carbon quaternary stereocenters in good ee and yield. Mechanistic studies provide strong support for a catalytic cycle that involves activation of both the electrophile (anhydride → acylpyridinium) and the nucleophile (silyl ketene acetal → enolate).
An Improved and Convenient Synthesis of Esters Using 1,1'-Carbonyldiimidazole and a Reactive Halide
Kamijo, Tetsuhide,Harada, Hiromu,Iizuka, Kinji
, p. 5044 - 5047 (2007/10/02)
The esterification of carboxylic acid proceeded easily in a one-pot reaction with 1,1'-carbonyldiimidazole in the presence of a reactive halide under neutral reaction conditions in high yields. Keywords - esterification: 1,1'-carbonyldiimidazole; formylation; tert-butyl ester; imidazolium salt; one-pot reaction
