Synthesis of macrocyclic α-amino esters through the chemoselective hydrolysis of benzoxazinephanes

The role of non-covalent interactions in 4-hydroxybenzylamine macrocyclisation: computational and synthetic evidence

“…Such hydrolysis is characteristic of the benzoxazines and occurs easily for benzoxazinic azacyclophanes. 29,30 The second peak (0.…”

Diphosphametacyclophanes: Structural and Electronic Influences of Substituent Variation within a Family of Bis(diketophosphanyl) Macrocycles

“…Cyclophanes in general are a well-established class of macrocycle with numerous applications, including molecular recognition and host–guest chemistry, selective asymmetric synthesis and catalysis, biomimetics, and more recently molecular electronics . Within many of these roles the incorporation of donor atoms is desirable, whether as appended functionalities (e.g., exocyclic phosphanes, phosphates, and amines) or as bridging units within the macrocyclic core, such as in the poly­(thia)- and poly­(aza)-cyclophanes . Synthetically, the latter typically require prolonged, multistep, and/or aggressive protocols, to which one might reasonably attribute the essential neglect of analogues incorporating endocyclic phosphorus moieties.…”

Facile self-assembly of the first diphosphametacyclophane

“…poly(thia) or poly(aza) cyclophanes. 5 However, notably absent from this selection are phosphacyclophanes, despite the considerable impetus to explore the phosphorus/nitrogen and phosphorus/carbon analogies, and a prevalence of other phosphorus heterocycles that often incorporate an aromatic unit as part of the cyclic skeleton. 6 Herein, we report the facile synthesis of the first such compound, and preliminary investigation of its coordination chemistry.…”