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
收藏
页码：2099 / 2102
页数：4
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