Poelloth, Benjamin published the artcileThe Size-Accelerated Kinetic Resolution of Secondary Alcohols, Application of Pyrene-2-carboxylic acid, the main research area is secondary alc kinetic resolution acylation side chain size enantioselectivity; acylation; asymmetric catalysis; kinetic resolution; molecular recognition; noncovalent interactions.
The factors responsible for the kinetic resolution of alcs. by chiral pyridine derivatives have been elucidated by measurements of relative rates for a set of substrates with systematically growing aromatic side chains using accurate competitive linear regression anal. Increasing the side chain size from Ph to pyrenyl results in a rate acceleration of more than 40 for the major enantiomer. Based on this observation a new catalyst with increased steric bulk has been designed that gives enantioselectivity values of up to s=250. Extensive conformational anal. of the relevant transition states indicates that alc. attack to the more crowded side of the acyl-catalyst intermediate is favored due to stabilizing CH-π-stacking interactions. Exptl. and theor. results imply that enantioselectivity enhancements result from accelerating the transformation of the major enantiomer through attractive non-covalent interactions (NCIs) rather than retarding the transformation of the minor isomer through repulsive steric forces.
Angewandte Chemie, International Edition published new progress about Acylation catalysts (stereoselective). 36428-96-3 belongs to class chlorides-buliding-blocks, name is Pyrene-2-carboxylic acid, and the molecular formula is C17H10O2, Application of Pyrene-2-carboxylic acid.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics