Enantioselective Organocatalytic Synthesis of Arylglycines via Friedel-Crafts Alkylation of Arenes with a Glyoxylate Imine

被引：69

作者：

Enders, Dieter ^{[1
]}

Seppelt, Matthias ^{[1
]}

Beck, Tobias ^{[2
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

[2] Univ Gottingen, Dept Struct Chem, D-37077 Gottingen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 09期

关键词：

amino acids; Bronsted acids; Friedel-Crafts reaction; organocatalysis; phosphoric acids; ALPHA-AMINO-ACIDS; CHIRAL PHOSPHORIC-ACID; HIGHLY DIASTEREOSELECTIVE SYNTHESIS; DIELS-ALDER REACTIONS; ASYMMETRIC-SYNTHESIS; (3-INDOLYL)GLYCINE DERIVATIVES; CATALYZED ADDITION; ARYLBORONIC ACIDS; BRONSTED ACID; ENE REACTIONS;

D O I：

10.1002/adsc.201000143

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The enantioselective organocatalytic synthesis of arylglycines has been developed employing 1 mol% of an enantiopure N-triflyl phosphoramide Bronsted acid as organocatalyst. Various differently substituted phenylglycine derivatives can be synthesized in good to excellent yields and enantiomeric excesses based on a Friedel-Crafts alkylation of electron-rich arenes with a glyoxylate imine. A novel protocol for the deprotection of the N-tert-butylsulfonyl (Bus) group has also been developed.

引用

页码：1413 / 1418

页数：6

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