Synthesis And Application Of Chiral Thermocarbamate Compounds

The homoallylic and homopropargylic amines are very important structural units due primarily to their widespread use as crucial intermediates for the synthesis of pharmaceutical compounds as well as their presence in a number of biologically active compounds as the key skeleton. This dissertation mainly focuses on the study of allylation and propargylation of chiral N-tert-butanesulfinyl imines with multi-substituted allyl bromides and synthesis of trans-multi-substituted indolines and tetrahydroquinolines via intramolecular C-N cross-coupling of homoallylic amines.In the first and second parts, an efficient and practical approach has been developed to synthesis of homoallylic and homopropargylic amines with quaternary stereocenters in favourable yields and stereoselectivity under mind conditions. Not only aryl ketimines but also aliphatic ketimines provided good results. Particularly, this method could be harnessed to obtain β-amino alcohols that contain quaternary stereocentersIn the third and fourth parts, we have developed a highly efficient approach to synthesis of trans-multi-substituted indolines and tetrahydroquinolines in favourable yields and stereoselectivities under mild conditions. Especially, tetrahydroquinolines with quaternary stereocenters could be prepared readily from the N-tert-butanesulfinyl ketimines. Notably, using this method, a deal of key scaffold in a variety of pharmaceutical compounds and biologically active compounds could be readily prepared. We are expecting their wide applications in organic synthesis and pharmaceutical industry.