A Bifunctional Cyclopropeneimine with a Tunable Hydrogen-Bond Donating Group and Its Application in the Enantioselective Synthesis of α,β-Diamino Phosphonates.

ABSTRACT: Lambert and co-workers have developed several chiral bases using a cyclopropeneimine as the basic moiety. Typically, these catalysts have a pendant hydroxyl group which acts as a hydrogen-bond donor and activates the electrophile. In catalysts with a hydrogen-bond donor, prior work from the Sigman group has shown that the acidity of the donor plays an important role in imparting selectivity. However, in the case of cyclopropeneimines reported by Lambert and co-workers, the acidity of the pendant arm is not easily tunable. To address this, we have developed a cyclopropeneimine catalyst with cyclohexanediamine as the chiral scaffold. One of the amino groups on the cyclohexanediamine is part of the cyclopropeneimine moiety, while the other is functionalized with an acyl group. The acidity of

SUBMITTER: Chittoory AK 

PROVIDER: S-EPMC12409684 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature