Efficient monoacylation of symmetrical secondary alkanediamines and synthesis of unsymmetrical diacylated alkanediamines. A new L-proline-based organocatalyst

Article abstract of DOI:10.24820/ark.5550190.p011.054

A simple procedure was developed for the monoacylation of several unprotected alkanediamines with carboxylic acids by using PyBOP-HOBt as coupling agent in the presence of DIEA at room temperature. Yields were moderate with primary alkanediamines and good to excellent with linear or cyclic secondary ones. To illustrate the utility of these monoacylated products, six unsymmetrical diacylated alkanediamines were synthesized. In addition, one of these compounds was evaluated as organocatalyst in an asymmetric aldol reaction. R' R' NHR O R _N O R _N PyBOP, HOBt PyBOP, HOBt DIEA, DMF DIEA, DMF NHR NHR O N O 10 equiv O R 11 exemples R' R = H, alkyl R'' OH 67-95% yield R'' OH 6 exemples