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Screening for generality in asymmetric catalysis
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Journal Article
Screening for generality in asymmetric catalysis
2022
Overview
Research in the field of asymmetric catalysis over the past half century has resulted in landmark advances, enabling the efficient synthesis of chiral building blocks, pharmaceuticals and natural products
1
–
3
. A small number of asymmetric catalytic reactions have been identified that display high selectivity across a broad scope of substrates; not coincidentally, these are the reactions that have the greatest impact on how enantioenriched compounds are synthesized
4
–
8
. We postulate that substrate generality in asymmetric catalysis is rare not simply because it is intrinsically difficult to achieve, but also because of the way chiral catalysts are identified and optimized
9
. Typical discovery campaigns rely on a single model substrate, and thus select for high performance in a narrow region of chemical space. Here we put forth a practical approach for using multiple model substrates to select simultaneously for both enantioselectivity and generality in asymmetric catalytic reactions from the outset
10
,
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. Multisubstrate screening is achieved by conducting high-throughput chiral analyses by supercritical fluid chromatography–mass spectrometry with pooled samples. When applied to Pictet–Spengler reactions, the multisubstrate screening approach revealed a promising and unexpected lead for the general enantioselective catalysis of this important transformation, which even displayed high enantioselectivity for substrate combinations outside of the screening set.
The analytical workflow outlined in this study allows multiple crude reaction mixtures to be analysed simultaneously, with substantial reductions in method development and analysis time, and maximizes the chances of finding catalytic systems with broad substrate scope.
Publisher
Nature Publishing Group UK,Nature Publishing Group
Subject
/ Biological Products - chemical synthesis
/ Biological Products - chemistry
/ Chemistry Techniques, Synthetic - methods
/ Chromatography, Supercritical Fluid
/ Humanities and Social Sciences
/ Methods
/ Pharmaceutical Preparations - chemical synthesis
/ Pharmaceutical Preparations - chemistry
/ Science
