Facilitated inversion complicates the stereodynamics of an SN2 reaction at nitrogen center

Multiple-inversion, the analogue of the double-inversion pathway recently revealed for SN2@C, is the key mechanism in SN2 at N center undermining stereospecificity.

Photoinduced Remote Heteroaryl Migration Accompanied by the Cyanoalkylacylation in Continuous Flow

A photoinduced 1,4-heteroaryl migration from a carbon center to a nitrogen center accompanied by a cyanoalkylacylation of heterocyclic-substituted azidyl homoallylic alcohols and cycloketone oxime esters, is described. This simple and...

Site-specific catalytic activities to facilitate solvent-free aerobic oxidation of cyclohexylamine to cyclohexanone oxime over highly efficient Nb-modified SBA-15 catalysts

The development of highly active and selective heterogeneous catalysts for efficient oxidation of cyclohexylamine to cyclohexanone oxime is a challenge associated with the highly sensitive nitrogen center of cyclohexylamine.

FR901483: Synthetic Efficiency Remains a Challenge

FR901483 is a unique alkaloid bearing an aza-tricyclic structure, a phosphate group, and a congested tertiary nitrogen center. This alkaloid was reported to be a potent immunosuppressant with antimetabolite ability. The unprecedented architecture has captured imagination of synthetic chemists since its isolation in 1996. To date, ten total or formal syntheses and several synthetic approaches to access the tricyclic core skeleton have been reported. In this review, we highlight the novel synthetic methods and strategies and discuss the synthetic challenge for meeting the criteria of drug development.1 Introduction2 Bioinspired Total Synthesis of FR9014833 Non-bioinspired Approaches toward FR9014834 Various Tactics for Accessing the Core Skeleton5 Challenges for Efficiency

Newly proposed proton-abstraction roundabout with backside attack mechanism for the SN2 reaction at the nitrogen center in F− + NH2Cl

Two novel reaction mechanisms are revealed for the SN2 reaction at the nitrogen center in the F− + NH2Cl reaction.