Construction of axially chiral compounds via asymmetric organocatalysis

YB Wang, B Tan - Accounts of chemical research, 2018 - ACS Publications
Conspectus Axially chiral compounds have received much attention from chemists because
of their widespread appearance in natural products, biologically active compounds, and …

Asymmetric catalysis mediated by synthetic peptides, version 2.0: expansion of scope and mechanisms

AJ Metrano, AJ Chinn, CR Shugrue, EA Stone… - Chemical …, 2020 - ACS Publications
Low molecular weight synthetic peptides have been demonstrated to be effective catalysts
for an increasingly wide array of asymmetric transformations. In many cases, these peptide …

Peptide-based catalysts reach the outer sphere through remote desymmetrization and atroposelectivity

AJ Metrano, SJ Miller - Accounts of Chemical Research, 2018 - ACS Publications
Conspectus Nature's catalytic machinery has provided endless inspiration for chemists.
While the enzymatic ideal has yet to be fully realized, the field has made tremendous strides …

Applications of nonenzymatic catalysts to the alteration of natural products

CR Shugrue, SJ Miller - Chemical reviews, 2017 - ACS Publications
The application of small molecules as catalysts for the diversification of natural product
scaffolds is reviewed. Specifically, principles that relate to the selectivity challenges intrinsic …

Catalytic dynamic kinetic resolutions in tandem to construct two-axis terphenyl atropisomers

OM Beleh, E Miller, FD Toste… - Journal of the American …, 2020 - ACS Publications
The defined structure of molecules bearing multiple stereogenic axes is of increasing
relevance to materials science, pharmaceuticals, and catalysis. However, catalytic …

Diversity of secondary structure in catalytic peptides with β-turn-biased sequences

AJ Metrano, NC Abascal, BQ Mercado… - Journal of the …, 2017 - ACS Publications
X-ray crystallography has been applied to the structural analysis of a series of tetrapeptides
that were previously assessed for catalytic activity in an atroposelective bromination …

Asymmetric Allylic Substitution‐Isomerization for the Modular Synthesis of Axially Chiral N‐Vinylquinazolinones

JY Zou, YY Yang, J Gu, F Liu, Z Ye, W Yi… - Angewandte …, 2023 - Wiley Online Library
Axially chiral N‐substituted quinazolinones are important bioactive molecules, which are
presented in many synthetic drugs. However, most strategies toward their atroposelective …

A combined DFT, energy decomposition, and data analysis approach to investigate the relationship between noncovalent interactions and selectivity in a flexible …

E Miller, BK Mai, JA Read, WC Bell, JS Derrick… - ACS …, 2022 - ACS Publications
Developing strategies to study reactivity and selectivity in flexible catalyst systems has
become an important topic of research. Herein, we report a combined experimental and …

Conformational dynamics in asymmetric catalysis: is catalyst flexibility a design element?

JM Crawford, MS Sigman - Synthesis, 2019 - thieme-connect.com
Traditionally, highly selective low molecular weight catalysts have been designed to contain
rigidifying structural elements. As a result, many proposed stereochemical models rely on …

Peptide‐Catalyzed Fragment Couplings that Form Axially Chiral Non‐C2‐Symmetric Biaryls

G Coombs, MH Sak, SJ Miller - Angewandte Chemie, 2020 - Wiley Online Library
We have demonstrated that small, modular, tetrameric peptides featuring the Lewis‐basic
residue β‐dimethylaminoalanine (Dmaa) are capable of atroposelectively coupling …