The Many Roles of Quantum Chemical Predictions in Synthetic Organic Chemistry

Abstract

This account discusses representative case studies for various applications of quantum chemical calculations in synthetic organic chemistry. These include confirmation of target structures, methodology development, and catalyst design. These examples demonstrate how predictions from quantum chemical calculations can be utilized to streamline synthetic efforts.

Predicting New Ugi–Smiles Couplings: A Combined Experimental and Theoretical Study

“…This study brings a further demonstration of the value of merging experimental and theoretical methods to progress the study of new reactions. [15] The Ugi-Smiles coupling was initially discovered trying to combine Smiles rearrangements with Ugi couplings. The choice of the phenols was then mainly dictated by their previous use in Smiles rearrangements.…”

Synthesis and Utility of Dihydropyridine Boronic Esters

“…Ther elative stereochemistry was initially assigned by comparison of experimental 1 Ha nd 13 C chemical shifts with those computed for possible diastereomers using quantum chemical methods [mPW1PW91/6-311 + G(2d,p)//M06-2X/6-31 + G(d,p), scaled]. [23] Thestructure was later confirmed by X-ray crystallography,thus indicating that DFT methods can be used for other products for which crystallography is not feasible.…”

Density functional theory studies of Hypaphorine from Erythrina mildbraedii and Erythrina addisoniae: structural and biological properties

“…root hair formation and stimulates curling of the roots which aids in these symbiotic relationships [7]. Hypaphorine has thus been detected in a number of ectomycorrhizal fungal species like Pisolithus tinctorius [1,11,12]. In these symbiotic relationships, hypaphorine inhibits the effect of IAA in the fungi by blocking membrane-bound IAA receptors thus inducing abnormal proliferation of hyphae that extend intracellularly into plant tissues.…”