posted on 2024-02-22, 18:45authored byTeng-Zhao Xiong, Nuermaimaiti Yisimayili, Chong-Dao Lu
Enamine and iminium ion-mediated asymmetric organocatalysis
was
not successful in achieving highly stereoselective α-chlorination
of acyclic α,α-disubstituted carbonyls. To address this
limitation, an alternative method was developed, which involved the
use of geometry-defined persubstituted enesulfinamides to intercept
the electrophilic chlorinating reagent. This approach enables the
asymmetric construction of challenging acyclic α,α-disubstituted
α-chlorinated ketimines with a high degree of stereoselectivity.
The use of chloramine-T, a cost-effective and stable chlorine source
rarely utilized in asymmetric electrophilic chlorination, plays a
crucial role in achieving superior stereocontrol.