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钯催化由乙醛酸、磺酰胺和芳基三氟硼酸盐对映选择性合成α-芳基甘氨酸衍生物

Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates.

作者信息

Jakob Bastian, Schneider Nico, Gengenbach Luca, Manolikakes Georg

机构信息

Department of Chemistry, RPTU Kaiserslautern-Landau, Erwin-Schrödinger-Str. Geb. 54, D-67663 Kaiserslautern, Germany.

出版信息

Beilstein J Org Chem. 2023 May 25;19:719-726. doi: 10.3762/bjoc.19.52. eCollection 2023.

DOI:10.3762/bjoc.19.52
PMID:37284589
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10241097/
Abstract

A palladium-catalyzed enantioselective three-component reaction of glyoxylic acid, sulfonamides and aryltrifluoroborates is described. This process provides modular access to the important α-arylglycine motif in moderate to good yields and enantioselectivies. The formed α-arylglycine products constitute useful building blocks for the synthesis of peptides or arylglycine-containing natural products.

摘要

描述了一种钯催化的乙醛酸、磺酰胺和芳基三氟硼酸盐的对映选择性三组分反应。该过程以中等至良好的产率和对映选择性提供了模块化合成重要的α-芳基甘氨酸基序的方法。所形成的α-芳基甘氨酸产物是用于合成肽或含芳基甘氨酸的天然产物的有用构建块。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/fdc2f45f6dcf/Beilstein_J_Org_Chem-19-719-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/e67cdec4c837/Beilstein_J_Org_Chem-19-719-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/5264091afb88/Beilstein_J_Org_Chem-19-719-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/67dbd2cdfeaa/Beilstein_J_Org_Chem-19-719-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/46b12bf7bf87/Beilstein_J_Org_Chem-19-719-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/a5729634f446/Beilstein_J_Org_Chem-19-719-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/fdc2f45f6dcf/Beilstein_J_Org_Chem-19-719-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/e67cdec4c837/Beilstein_J_Org_Chem-19-719-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/5264091afb88/Beilstein_J_Org_Chem-19-719-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/67dbd2cdfeaa/Beilstein_J_Org_Chem-19-719-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/46b12bf7bf87/Beilstein_J_Org_Chem-19-719-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/a5729634f446/Beilstein_J_Org_Chem-19-719-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b95/10241097/fdc2f45f6dcf/Beilstein_J_Org_Chem-19-719-g007.jpg

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Org Lett. 2016 Aug 19;18(16):4116-9. doi: 10.1021/acs.orglett.6b02045. Epub 2016 Aug 9.
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