Design of a Dual Hydrogen-Bonding Bisamidinium Catalyst

Significance

An efficient way of designing a catalyst is presented. The authors calculated the optimal orientation of an amide N-H bond with di­methyl ether. These optimal bond properties were then used as vectors for the database mining program CAVEAT^a revealing several templating substructures from the Cambridge Crystal Structure Database. Inspired by these structures the authors synthesized bisamidinium salt 1 in six steps. The primary design feature is a dual hydrogen-bonding array for monodentate substrates.

^a CAVEAT V2.2; P. A. Bartlett, University of California, Berkeley.