Synthesis of 4-fluoro-β-(4-fluorophenyl)-L-phenylalanine by an asymmetric phase-transfer catalyzed alkylation:: Synthesis on scale and catalyst stability

被引：38

作者：

Patterson, Daniel E. ^{[1
]}

Xie, Shiping ^{[1
]}

Jones, Lynda A. ^{[1
]}

Osterhout, Martin H. ^{[1
]}

Henry, Christopher G. ^{[1
]}

Roper, Thomas D. ^{[1
]}

机构：

[1] GlaxoSmithKline, Chem Dev, Res Triangle Pk, NC 27709 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2007年 / 11卷 / 03期

关键词：

D O I：

10.1021/op060190j

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

4-Fluoro-beta-(4-fluorophenyl)-L-phenylalanine 1 was synthesized by the asymmetric phase- transfer catalyzed alkylation of tertbutyl glycinate-benzophenone Schiff base using the cinchona alkaloid derived catalyst 6. Upon scaling, it was observed that to achieve high levels of enantioselectivity, it was necessary to add the catalyst or base last. From these studies, insight into the stability of the catalyst 6 under the reaction conditions was gained.

引用

页码：624 / 627

页数：4

共 33 条

[1]

BEYLIN V, 1993, Patent No. 5198548

[2] Palladium-catalyzed allylic alkylation of tert-butyl(diphylmethylene)-glycinate with simple allyl esters under chiral phase transfer conditions [J].

Chen, GS ;

Deng, YJ ;

Gong, LZ ;

Mi, AQ ;

Cui, X ;

Jiang, YZ ;

Choi, MCK ;

Chan, ASC .

TETRAHEDRON-ASYMMETRY, 2001, 12 (11) :1567-1571

[3] Highly enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent; applications and mechanism [J].

Corey, EJ ;

Bo, YX ;

Busch-Petersen, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :13000-13001

[4] Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst [J].

Corey, EJ ;

Noe, MC ;

Xu, F .

TETRAHEDRON LETTERS, 1998, 39 (30) :5347-5350

[5]

Corey EJ, 1999, ANGEW CHEM INT EDIT, V38, P1931, DOI 10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO

[6]

2-4

[7] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].

Corey, EJ ;

Xu, F ;

Noe, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415

[8] EFFICIENT CATALYTIC ASYMMETRIC ALKYLATIONS .1. ENANTIOSELECTIVE SYNTHESIS OF (+)-INDACRINONE VIA CHIRAL PHASE-TRANSFER CATALYSIS [J].

DOLLING, UH ;

DAVIS, P ;

GRABOWSKI, EJJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) :446-447

[9] ELECTROPHILIC AZIDE TRANSFER TO CHIRAL ENOLATES - A GENERAL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

EVANS, DA ;

BRITTON, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (22) :6881-6883

[10]

GASCOYNE JM, 1977, J CHEM SOC P1, V8, P1051

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