A Convenient Method for the Asymmetric Synthesis of Fluorinated α-Amino Acids from Alcohols

被引：19

作者：

Drouet, Fleur ^{[1
,2
]}

Noisier, Anais F. M. ^{[1
,2
]}

Harris, Craig S. ^{[3
]}

Furkert, Daniel P. ^{[1
,2
]}

Brimble, Margaret A. ^{[1
,2
]}

机构：

[1] Univ Auckland, Sch Chem Sci, Auckland Cent 1042, New Zealand

[2] Univ Auckland, Maurice Wilkins Ctr Mol Biodiscovery, Auckland Cent 1042, New Zealand

[3] Galderma R&D, F-06410 Biot, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 06期

关键词：

Asymmetric synthesis; Fluorine; Alcohols; Amino acids; NI(II) COMPLEXES; NICKEL(II) COMPLEXES; GLYCINE; HOMOLOGATION; PEPTIDE;

D O I：

10.1002/ejoc.201301718

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Due to their numerous applications, fluorinated amino acids have recently attracted significant attention. The preparation of fluorine-containing phenylalanines, heteroaryl alanines and aliphatic fluorinated amino acids using Mitsunobu-Tsunoda alkylation of a chiral nucleophilic glycine equivalent with readily available alcohol substrates is described. The reaction proceeds in high yields and with excellent diastereoselectivity. This method provides an efficient synthetic route to fluorinated amino acids for which asymmetric approaches are scarce.

引用

页码：1195 / 1201

页数：7

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