Sui Generis Helicene-Based Supramolecular Chirogenic System: Enantioselective Sensing, Solvent Control, and Application in Chiral Group Transfer Reaction.

ABSTRACT: A novel dioxa[6]helicene-based supramolecular chirogenic system (1) as a specific chiral recognition host for enantiopure trans-1,2-cyclohexanediamine (2) is reported. Host 1 with an inherent free phenolic group and a (1S)-camphanate chiral handle on the opposite terminal rings of the helicene chromophore acted as an efficient turn on fluorescent sensor for S,S-2 with an excellent enantioselective factor, α = K _SS /K _RR = 6.3 in benzene. This specific host-guest interaction phenomenon is found to be solvent-dependent, which leads to an enantioselective chiral (camphanate) group transfer to the diamine guest molecule. In the case of R,R-2, the de value is up to 68%

SUBMITTER: Hasan M 

PROVIDER: S-EPMC6641162 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature