Application of Bidentate Oxazoline Carbene Ligands with Planar and Central Chirality in Asymmetric beta-Boration of alpha,beta-Unsaturated Esters

作者:Niu Zonghong; Chen Jianqiang; Chen Zhen; Ma Manyuan; Song Chun*; Ma Yudao
来源:Journal of Organic Chemistry, 2015, 80(1): 602-608.
DOI:10.1021/jo5021135

摘要

A series of new oxazoline-substituted imidazolium salts based on [2.2]paracyclophane were synthesized and characterized. The new bidentate oxazoline-carbene precursor with planar and central chirality had significant advantage than the bicyclic 1,2,4-triazolium salt derived from [2.2]paracyclophane as a monodentate carbene ligand in Cu(I)-catalyzed asymmetric beta-boration of alpha,beta-unsaturated esters, giving the desired products in high enantioselectivities and yields.