Addition of isobutyraldehyde to 1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane (mother diamine) cleanly gives a stable, fused imidazolidine-dihydro-1,3-oxazine ring complex. However, vigorous heating of the fused ring complex gives the diaza-Cope rearrangement product with excellent yield and stereoselectivity. A variety of alkyl aldehydes have been used to make corresponding alkyl diamines with excellent yield and stereospecificity. DFT computation shows that the intrinsic barrier for the rearrangement involving alkyl imines is about 7.9 kcal/mol greater than that involving aryl imines.
Research. Development. Production.
We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.