Asymmetric Organocatalyzed Synthesis of α-Aminophosphinates via Thiourea Anion-Binding Catalysis

被引：4

作者：

Niland, Caoimhe J. ^{[1
,2
]}

Ruddy, Joseph J. ^{[1
]}

O'Fearraigh, Martin P. ^{[1
]}

Mcgarrigle, Eoghan M. ^{[1
,2
]}

机构：

[1] Univ Coll Dublin, Ctr Synth & Chem Biol, UCD Sch Chem, Dublin 4, Ireland

[2] Univ Coll Dublin, SFI Res Ctr Pharmaceut, UCD Sch Chem, Ctr Synth & Chem Biol,SSPC, Dublin 4, Ireland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 11期

关键词：

organocatalysis; anion-binding; organophosphorus; thiourea; asymmetric; BOND-DONOR CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; PHOSPHINE OXIDES; DIASTEREOSELECTIVE SYNTHESIS; PHOSPHORUS-COMPOUNDS; 1ST SYNTHESIS; H-BOND; ACCESS; HYDROGENATION; DEAROMATIZATION;

D O I：

10.1002/ejoc.202301212

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thioureas catalyze the reaction of phosphonites with in situ-generated isoquinolinium salts to give C and P-stereogenic alpha-aminophosphinates in high enantioselectivity (up to 96 %) and yield (up to 95 %). Low diastereoselectivity was obtained and this is rationalized in the context of a mechanistic proposal involving anion-binding catalysis of the P-C bond formation step followed by uncatalyzed Arbuzov collapse. The scope of the reaction, including a g-scale example, was demonstrated. P-Stereogenic alpha-aminophosphinates were obtained in high enantioselectivity via anion-binding catalysis with thiourea catalysts, further expanding the range of nucleophiles that can be used in this type of catalysis.+ image

引用

页数：6

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