Chirality manifests itself in molecular systems in which the kinetically accessible structural space shows no overlap with its mirror image. In most chiral molecules, this property is induced by a stereogenic element: often a multivalent chiral atom (point chirality) or a rotationally restricted bond, spiro atom or other structural element that creates an axis enforcing a non-planar arrangement of neighboring substituents (axial chirality) . In more complex scenarios, the conformational constraint from which chirality originates is induced by the spatial arrangement of atoms and the inherent geometry of the system, generating an emergent trait that cannot be traced back to local properties of individual atoms nor bonds. Molecules featuring these non-local stereogenic elements are often referred to as inherently chiral . Examples of systems featuring non-local stereogenic elements include helix-shaped molecules (helical chirality) , cyclophane atropisomers , organometallic sandwich complexes (planar chirality) , mechanically interlocked systems made up of achiral elements (mechanical chirality) or even kinetically stable molecular aggregates and hydrogen bonding networks (sometimes referred to as cyclochirality) . Although less prevalent, medium-sized rings can also showcase inherent chirality . This property can arise in simple organic molecules featuring rings of seven or more atoms with a high fraction of sp 2 constituents, leading to the kinetic stability of some specific conformations. Similarly to other atropisomers, thermal stereoisomerization of these compounds is possible via a sequence of concerted bond torsions. Often, chiral conformations of these medium-sized rings are bowl-shaped and their geometrical inversion pathway is reminiscent of that of trigonal pyramidal atoms . Examples of kinetically stable, inherently chiral sevenmembered heterocycles are the Muscarinic receptor antagonist telenzepine, where the (+)-isomer is up to 500 times more active than its enantiomer , and the pirenzepine derivative UH-AH 37 . Merck has also optimized a series of analogs of MK-7725 towards conformational rigidity, achieving inherently chiral scaffolds with excellent thermal stability which allows their study and development as single stereoisomers (Figure ) . Nevertheless, the obtainment of enantioenriched (or enantiopure) samples of any of these compounds had to rely on chiral separation techniques . Indeed, to our knowledge, the stereocontrolled cyclization of molecules whose only stereogenic element lies in an inherently chiral medium-sized ring is unknown. In this report, we describe a strategy that accomplishes this feat for both 7-membered and 8-membered ring systems. Notably, we achieve high levels of stereocontrol with a singular chiral catalyst for both transformations, via two distinct reaction mechanisms -SNAr and SN2. The muscarinic receptor antagonist telenzepine in one of its enantiomers (left) and one of Merck's analogs of MK-7725 (right), both possessing high configurational stability of the inherently chiral sevenmembered ring. b: Maximally preorganized disconnection strategy for the synthesis of challenging, strained ring systems. Different conformational biases of the cyclization substrates influence their relative tendencies to react intra-versus inter-molecularly. c: Generalizable tether cyclization strategy -the catalyst recognition elements are conserved and are responsible for catalyst binding across multiple ring sizes. d: Use of tertiary Nalkyl, N-aryl arylamides as s-cis conformational biases, and opposite conformational preferences of N-aryl arylamides. e: The choice of disconnection dictates the degree of substrate preorganization in cyclization reactions, and therefore their feasibility in the forward sense. f: Initial reaction optimization for the enantioselective SNAr cyclization to form dibenzodiazepinones.