Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc-Copper-Mediated SN2′ Alkylation

被引：17

作者：

Kobayashi, Kazuya ^{[1
]}

Narumi, Tetsuo ^{[1
]}

Oishi, Shinya ^{[1
]}

Ohno, Hiroaki ^{[1
]}

Fujii, Nobutaka ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 12期

关键词：

SOLID-PHASE SYNTHESIS; PEPTIDE ISOSTERES; STEREOSELECTIVE-SYNTHESIS; ORGANOCOPPER REAGENTS; ENKEPHALIN ANALOG; ALKENE-DIPEPTIDE; FACILE SYNTHESIS; (E)-ALKENE; FLUOROOLEFIN; INHIBITORS;

D O I：

10.1021/jo9005602

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthetic approach to Xaa-Yaa-type (Z)-trifluoromethylalkene dipeptide isostere (CF3-ADI) has been developed. Starting from readily available L-phenylalanine and L-alanine, several CF3-ADIs were obtained through nucleophilic trifluoromethylation of gamma-keto esters and S(N)2' alkylation of trifluoromethylated mesylates. The influence of a trifluoromethyl group on the diastereoselectivity of the S(N)2' reaction is also discussed.

引用

页码：4626 / 4629

页数：4

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