|Title:||Divergent and Scalable Synthesis of α-Hydroxy/Keto-β-amino Acid Analogues by the Catalytic Enantioselective Addition of Glyoxylate Cyanohydrin to Imines|
|Authors:||Nanjo, Takeshi https://orcid.org/0000-0002-5679-6701 (unconfirmed)|
Takemoto, Yoshiji https://orcid.org/0000-0003-1375-3821 (unconfirmed)
|Author's alias:||南條, 毅|
|Publisher:||American Chemical Society|
|Journal title:||ACS Catalysis|
|Abstract:||The catalytic enantioselective addition of glyoxylate cyanohydrin to imines to afford α-keto-β-amino acid equivalents is reported. Sterically tuned aminobenzothiadiazine catalysts provided high yields and stereoselectivities (up to 100% yield, 99% ee, >99:1 dr) for both aromatic and aliphatic imines, and the stereodivergent synthesis of both diastereomers was achieved. The optimal catalytic system was scalable, even with a low catalyst loading. The resulting adducts were converted into various chiral building blocks, including β-amino acid analogues, which are important motifs in medicinal chemistry, while maintaining a high enantiomeric excess.|
|Rights:||This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.9b03394.|
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This is not the published version. Please cite only the published version.
|Appears in Collections:||Journal Articles|
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