Non-Classical C–H···X Hydrogen Bonding and Its Role in Asymmetric Organocatalysis
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AbstractNon-classical hydrogen bonds (NCHBs) have attracted significant interest in the past decade particularly because of their important role in asymmetric catalytic systems. These weak interactions (< 4 kcal/mol) offer much flexibility in the preorganization of molecular entities required to achieve high enantioselectivity. Herein, we review some recent important organocatalytic asymmetric reactions where a NCHB serves as a critical factor in determining the stereoselectivity.
2 Hydrogen Bonds (HBs) and Non-Classical Hydrogen Bonds (NCHBs)
3 Early Developments in NCHBs
4 Selected Examples of NCHBs in Organic Transformations
5 Recent Examples of NCHBs in Enantioselective Reactions
6 Conclusions and Outlook
CitationHuang K-W, Ajitha M (2016) Non-Classical C–H···X Hydrogen Bonding and Its Role in Asymmetric Organocatalysis. Synthesis 48: 3449–3458. Available: http://dx.doi.org/10.1055/s-0035-1562475.
SponsorsThis work is supported by King Abdullah University of Science and Technology (KAUST).
PublisherThieme Publishing Group