Di(1‐naphthyl) methanol ester of carboxylic acids for absolute stereochemical determination

Abstract

The absolute stereochemistry of chiral carboxylic acids is determined as a di(1-naphthyl)methanol ester derivative. Computational scoring of conformations favoring either P or M helicity of the naphthyl groups, capable of exciton-coupled circular dichroic coupling, leads to a predicted stereochemistry for the derivatized carboxylic acids.

Absolute stereochemical determination of 1,2‐diols via complexation with dinaphthyl borinic acid

“…Furthermore, strong absorptions close to 200 nm, either from solvent and/or minute impurities, can diminish the short absorption band due to reduced signal/noise ratio. As observed in our previous studies with naphthyl substituted systems, 14,15 although two main transitions ( 1 La ~270 nm and 1 Bb ~220 nm) are present, there is no evidence of 1 La in the ECCD spectra, and only the coupling from the more intense 1 Bb band (long axis transition) is observed. The naphthyl substrate (R)-3 (entry 3) is note worthy, as addition of more than 1 equiv led to a complex CD spectrum with diminished amplitude.…”

“…The inspiration for the present work finds its origins not only from the work of others discussed above (converting acyclic diols into a cyclic derivative), but also in our recent work in which 1,1'-(bromomethylene) dinaphthalene (BDN) 14 and di(1naphthyl) methanol (DNM) 15 systems were used to determine the absolute stereochemistry of chiral amines and chiral carboxylic acids, respectively (Figure 2a,b). Derivatization of BDN and DNM with their respective asymmetric counterparts yields a system with a preferential helical arrangement of the naphthyl groups on the reporter.…”

Optical Activity and Helicity Enhancement of Highly Sensitive Dinaphthylmethane-Based Stereodynamic Probes for Secondary Alcohols

“…Recently, we and others have proven the utility of 1-naphthalene derivatives in stereochemical studies with the use of chiroptical methods. − For instance, Borhan used di­(1-naphthyl)­methanol esters for the determination of absolute stereochemistry of carboxylic acids. Although the results were spectacular, the studied objects were characterized by a low structural diversity …”

“…Although the results were spectacular, the studied objects were characterized by a low structural diversity. 77…”

Diasteroselective multi-component assemblies from dynamic covalent imine condensation and metal-coordination chemistry: mechanism and narcissistic stereochemistry self-sorting

“…Most of the times, this information is translated into a signal by the use of optical techniques such as circular dichroism (CD). 5 …”