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Conformational Control of Chiral Amido-Thiourea Catalysts Enables Improved Activity and Enantioselectivity.


ABSTRACT: While aryl pyrrolidinoamido-thioureas derived from ?-amino acids are effective catalysts in a number of asymmetric transformations, they exist as mixtures of slowly interconverting amide rotamers. Herein, the compromising role of amide bond isomerism is analyzed experimentally and computationally. A modified catalyst structure that exists almost exclusively as a single amide rotamer is introduced. This modification is shown to result in improved reactivity and enantioselectivity by minimizing competing reaction pathways.

SUBMITTER: Lehnherr D 

PROVIDER: S-EPMC5096793 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Conformational Control of Chiral Amido-Thiourea Catalysts Enables Improved Activity and Enantioselectivity.

Lehnherr Dan D   Ford David D DD   Bendelsmith Andrew J AJ   Kennedy C Rose CR   Jacobsen Eric N EN  

Organic letters 20160613 13


While aryl pyrrolidinoamido-thioureas derived from α-amino acids are effective catalysts in a number of asymmetric transformations, they exist as mixtures of slowly interconverting amide rotamers. Herein, the compromising role of amide bond isomerism is analyzed experimentally and computationally. A modified catalyst structure that exists almost exclusively as a single amide rotamer is introduced. This modification is shown to result in improved reactivity and enantioselectivity by minimizing co  ...[more]

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