Asymmetric Catalysis with a Mechanically Point-Chiral Rotaxane

作者：Cakmak Yusuf; Erbas Cakmak Sundus; Leigh David A^*

来源：Journal of the American Chemical Society, 2016, 138(6): 1749-1751.

DOI：10.1021/jacs.6b00303

Mechanical point-chirality in a [2]rotaxane is utilized for asymmetric catalysis. Stable enantiomers of the rotaxane result from a bulky group in the middle of the thread preventing a benzylic amide macrocycle shuttling between different sides of a prochiral center, creating point chirality in the vicinity of a secondary amine group. The resulting mechanochirogenesis delivers enantioselective organocatalysis via both enamine (up to 71:29 er) and iminium (up to 68:32 er) activation modes.

• 出版日期2016-2-17