Iridium complex-catalyzed highly enantio- and diastereoselective [2+2+2] cycloaddition for the synthesis of axially chiral teraryl compounds.
An asymmetric [2+2+2] cycloaddition of an alpha,omega-diyne, possessing ortho-substituted aryl groups on its terminus, and a monoalkyne with oxygen functionalities gave various axially chiral teraryl compounds. The coupling proceeded with extremely high enantio- (>99.5% ee) and diastereoselectivities (dl/meso = >95/5) when catalyzed by an iridium-chiral phosphine complex. As the products were readily transformed into diol compounds by deprotection without racemization, the present procedure provides access to a new chiral pool of diol compounds with C2 symmetry.
Shibata
Takanori
T
Department of Chemistry, School of Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan. tshibata@waseda.jp
Fujimoto
Takayoshi
T
Yokota
Kazuhisa
K
Takagi
Kentaro
K