The Synthesis of α,α-Disubstituted α-Amino Acids via Ichikawa Rearrangement

被引：25

作者：

Szczesniak, Piotr ^{[1
]}

Pieczykolan, Michal ^{[1
]}

Stecko, Sebastian ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 03期

关键词：

DIPEPTIDYL-PEPTIDASE-I; TO-ISOCYANATE REARRANGEMENT; NEUROTENSIN RECEPTOR ANTAGONIST; CATALYTIC ASYMMETRIC-SYNTHESIS; PURINERGIC P2X(7) RECEPTOR; N-HETEROCYCLIC CARBENES; CHIRAL ALLYLIC AMINES; STEREOSELECTIVE-SYNTHESIS; SIGMATROPIC REARRANGEMENT; MEDICINAL CHEMISTRY;

D O I：

10.1021/acs.joc.5b02628

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach to alpha,alpha-disubstituted alpha-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X(7)-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.

引用

页码：1057 / 1074

页数：18

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