As the tools of computational quantum chemistry have continued to mature, larger and more complex molecular systems have become amenable to computational study. However, studies of these complex systems often require the execution of enormous numbers of computations, which can be a tedious and error‐prone process if done manually. We have developed a suite of free, open‐source tools to facilitate the automation of quantum chemistry workflows. These tools are collected under the organization QChASM (Quantum Chemistry Automation and Structure Manipulation) and include functionality for building and manipulating complex molecular structures and performing routine tasks (AaronTools), a toolkit for automating TS optimizations and predictions of the outcomes of selective homogeneous catalytic reactions, and a plug‐in for UCSF ChimeraX that provides a graphical interface for building complex molecular structures and representing output from quantum chemistry computations. These tools are described below, with a focus on the recent Python implementation of AaronTools. This article is categorized under: Structure and Mechanism > Reaction Mechanisms and Catalysis Software > Quantum Chemistry

We report herein a rare example of enantiodivergent aldehyde addition with β-alkenyl allylic boronates via chiral Brønsted acid catalysis. 2,6-Di-9-anthracenyl-substituted chiral phosphoric acid-catalyzed asymmetric allylation using β-vinyl substituted allylic boronate gave alcohols with R absolute configuration. The sense of asymmetric induction of the catalyst in these reactions is opposite to those in prior reports. Moreover, in the presence of the same acid catalyst, the reactions with β-2-propenyl substituted allylic boronate generated homoallylic alcohol products with S absolute configuration. Unusual substrate-catalyst CÀ H•••π interactions in the favoured reaction transition state were identified as the origins of observed enantiodivergence through DFT computational studies.

Automated transiton state (TS) structure computations for a recently reported Pd-catalysed conjugated addition of arylboronic acids to 2-substituted chromones (Chem Sci, 2020, 11, 4602) reveal unexpected conformations of the key...

We report herein a rare example of enantiodivergent aldehyde addition with β-alkenyl allylic boronates via chiral Brønsted acid catalysis. 2,6-Di-9-anthracenyl-substituted chiral phosphoric acid-catalyzed asymmetric allylation using β-vinyl substituted allylic boronate gave alcohols with R absolute configuration. The sense of asymmetric induction of the catalyst in these reactions is opposite to those in prior reports. Moreover, in the presence of the same acid catalyst, the reactions with β-2-propenyl substituted allylic boronate generated homoallylic alcohol products with S absolute configuration. Unusual substrate-catalyst CÀ H•••π interactions in the favoured reaction transition state were identified as the origins of observed enantiodivergence through DFT computational studies.