Stereospecific Synthesis of Alkyl-Substituted Vicinal Diamines from the Mother Diamine: Overcoming the "Intrinsic Barrier" to the Diaza-Cope Rearrangement Reaction.

[摘要]：Addn. 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 were 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 ~7.9 kcal/mol greater than that involving aryl imines.

[全文传递流程]：

一般上传文献全文的时限在1个工作日内