A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters

被引：4

作者：

Albat, Dominik ^{[1
]}

Neudoerfl, Joerg-Martin ^{[1
]}

Schmalz, Hans-Guenther ^{[1
]}

机构：

[1] Univ Cologne, Dept Chem, Greinstr 4, D-50939 Cologne, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 14期

关键词：

Allylic substitution; Amino acid derivatives; Chiral phosphane ligands; Enantioselective catalysis; Palladium catalysis; ALLYLIC AMINATION; BUILDING-BLOCKS; DEHYDROGENASE; METALLOPHORE; ALKYLATIONS; LEAD;

D O I：

10.1002/ejoc.202100259

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereo-divergent synthesis of natural and unnatural opines in stereochemically pure form is based on the direct palladium-catalyzed N-allylation of alpha-amino acid esters (up to 97 % ee or 99 : 1 d.r.) using methyl (E)-2-penten-4-yl carbonate in the presence of only 1 mol% of a catalyst, prepared in-situ from the C-2-symmetric diphosphine iPr-MediPhos and [Pd(allyl)Cl](2). Selected target compounds (incl. a derivative of the drug enalapril) were efficiently obtained from the N-allylated intermediates by oxidative cleavage (ozonolysis) of the allylic C=C bond under temporary N-Boc-protection.

引用

页码：2099 / 2102

页数：4

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