Asymmetric Synthesis of Fmoc-Protected β-Hydroxy and β-Methoxy Amino Acids via a Sharpless Aminohydroxylation Reaction Using FmocNHCI

被引：10
|
作者：
Moreira, Ryan [1 ]
Taylor, Scott D. [1 ]
机构：
[1] Univ Waterloo, Dept Chem, 200 Univ Ave West, Waterloo, ON N2L 3G1, Canada
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 23期
基金：
加拿大自然科学与工程研究理事会;
关键词：
LIPOPEPTIDE ANTIBIOTIC COMPLEX; CARBOXYLIC-ACIDS; A54145; DERIVATIVES; DAPTOMYCIN; DISCOVERY;
D O I：
10.1021/acs.orglett.8b03458
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient asymmetric synthesis of L-threo-beta-hydroxyasparagine and L-threo-beta-methoxyaspartate that are suitably protected for Fmoc solid phase peptide synthesis is described. The key step in these syntheses was a Sharpless asymmetric aminohydroxylation reaction under basic conditions using N-chlorofluorenyl carbamate (FmocNHCl), a readily prepared and storable nitrogen source.
引用
收藏
页码：7717 / 7720
页数：4
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