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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  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-5679-6701 (unconfirmed)
Zhang, Xuan
Tokuhiro, Yusuke
Takemoto, Yoshiji  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0003-1375-3821 (unconfirmed)
Author's alias: 南條, 毅
徳弘, 佑介
竹本, 佳司
Keywords: asymmetric synthesis
organocatalysis
β-amino acid
cyanohydrin
diastereodivergent synthesis
Issue Date: 1-Nov-2019
Publisher: American Chemical Society
Journal title: ACS Catalysis
Volume: 9
Issue: 11
Start page: 10087
End page: 10092
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.
The full-text file will be made open to the public on 2 October 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
This is not the published version. Please cite only the published version.
URI: http://hdl.handle.net/2433/244716
DOI(Published Version): 10.1021/acscatal.9b03394
Appears in Collections:Journal Articles

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