55067-22-6Relevant academic research and scientific papers
General solvent-free highly selective N-tert-butyloxycarbonylation strategy using protic ionic liquid as an efficient catalyst
Majumdar, Swapan,De, Jhinuk,Chakraborty, Ankita,Maiti, Dilip K.
, p. 24544 - 24550 (2014/07/07)
A simple, rapid and solvent-free protocol is described for the chemo-selective transformation of amines to tert-butyloxycarbonyl protected derivatives (NHBoc) using Boc2O and imidazolium trifluoroacetate protic ionic liquid (5-20 mol%). Unwanted side products such as isocyanate, urea or N,N-di-Boc were not detected. The scope of the protection strategy was successfully explored for substrate alcohols, phenols and thiol at elevated temperatures. Optically pure amino acids, amino acid esters and amino alcohols were efficiently converted to the corresponding N-Boc protected derivatives in excellent yields without racemization at the chiral center. The distinct advantages of this method are: operational simplicity, cleaner reaction, high selectivity, excellent yield, rapid reaction convergence, easy preparation and recyclability of the catalyst.
A simple acylation of thiols with anhydrides
Temperini, Andrea,Annesi, Diego,Testaferri, Lorenzo,Tiecco, Marcello
supporting information; experimental part, p. 5368 - 5371 (2010/10/20)
Different thiols were efficiently acylated at room temperature with different anhydrides in the presence of potassium carbonate. Chemoselective protection of thiol in the presence of hydroxy group was achieved using di-tert-butyl dicarbonate and isatoic anhydride.
SULFUR-ASSISTED O-CARBONYLATION OF ALCOHOLS WITH CARBON MONOXIDE IN THE PRESENCE OF DBU
Mizuno, Takumi,Nishiguchi, Ikuzo,Hirashima, Tsuneaki,Ogawa, Akiya,Kambe, Nobuaki,Sonoda, Noboru
, p. 4767 - 4768 (2007/10/02)
The first example of sulfur-assisted O-carbonylation is described.Alcohols react with carbon monoxide, elemental sulfur, and alkyl halides in the presence of DBU to give S-alkyl carbonothioates selectively in good to excellent yields.
