11Binaphthylderived

11Binaphthylderived compounds refer to chemical species based on the binaphthyl scaffold in which substitutions are introduced at the 11-position of the framework. The designation is used in specialized literature to describe derivatives that explore axial chirality and steric tuning around the biaryl axis. Like other binaphthyl-based motifs (for example BINOL and BINAP), 11Binaphthylderived structures serve as chiral scaffolds in synthesis and materials science.

Structure and stereochemistry: The binaphthyl core consists of two naphthalene rings linked to create an atropisomeric axis. Substitution at the 11-position modifies the peri environment and can influence the preferred twist of the biaryl axis, altering enantioselectivity in catalytic applications and affecting the physical properties of the molecule.

Synthesis: Access typically proceeds from known binaphthyl precursors. Methods include regioselective lithiation or directed cross-coupling (such as Suzuki–Miyaura or Kumada) at the 11-position, followed by functional group transformations to install aryl, alkyl, or heteroatom substituents. Protecting group strategies may be used to preserve sensitive functionalities.

Applications: The 11-substituted derivatives are explored as enantioenriched ligands for asymmetric catalysis, including hydrogenation and cross-coupling, and as chiral building blocks in organocatalysis and materials chemistry. Substituent choice at 11 can tune steric encumbrance and electronic properties to optimize selectivity and reactivity.

Examples and scope: Reported substitutions span simple alkyl and aryl groups to more complex heteroatom-containing moieties. The field emphasizes structure–activity relationships around axial chirality and reports of BINAP-like performance with novel 11-substituted binaphthyl derivatives. See also BINAP, BINOL.