Stereoselective synthesis of anti-β-hydroxy-α-amino acids through dynamic kinetic resolution

被引：112

作者：

Makino, K ^{[1
]}

Goto, T ^{[1
]}

Hiroki, Y ^{[1
]}

Hamada, Y ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 07期

关键词：

amino acids; asymmetric synthesis; hydrogenation; kinetic resolution; ruthenium;

D O I：

10.1002/anie.200353072

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Upping the anti: Asymmetric anti-selective hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution has been achieved for the first time by using the Ru-binap catalyst. The reaction affords important anti-β-hydroxy-α-amino acids with 74-98% ee and high diastereomeric ratio in excellent yields (see scheme; binap = 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl).

引用

页码：882 / 884

页数：3

共 38 条

[1] Stereodivergent approach to β-hydroxy α-amino acids from C2-symmetrical alk-2-yne-1,4-diols [J].

Amador, M ;

Ariza, X ;

Garcia, J ;

Sevilla, S .

ORGANIC LETTERS, 2002, 4 (25) :4511-4514

[2] Asymmetric synthesis of all isomers of α-methyl-β-phenylserine [J].

Avenoza, A ;

Cativiela, C ;

Corzana, F ;

Peregrina, JM ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 2000, 11 (10) :2195-2204

[3]

CALDWELL CG, 1990, SYNTHESIS-STUTTGART, P34

[4]

COREY EJ, 1992, TETRAHEDRON LETT, V33, P6735

[5] An efficient synthesis of (2S,3R)-3-hydroxylysine via ruthenium catalyzed asymmetric hydrogenation [J].

Coulon, E ;

Cristina, M ;

de Andrade, C ;

Ratovelomanana-Vidal, V ;

Genêt, JP .

TETRAHEDRON LETTERS, 1998, 39 (36) :6467-6470

[6]

Evans D.A., 2001, ANGEW CHEM INT EDIT, V113, P1936, DOI DOI 10.1021/acs.oprd.5b00191

[7]

Evans DA, 2001, ANGEW CHEM INT EDIT, V40, P1884, DOI 10.1002/1521-3773(20010518)40:10<1884::AID-ANIE1884>3.0.CO

[8]

2-9

[9] ASYMMETRIC-SYNTHESIS - PRACTICAL PRODUCTION OF D-THREONINE AND L-THREONINE - DYNAMIC KINETIC RESOLUTION IN RHODIUM AND RUTHENIUM CATALYZED HYDROGENATION OF 2-ACYLAMINO-3-OXOBUTYRATES [J].

GENET, JP ;

PINEL, C ;

MALLART, S ;

JUGE, S ;

THORIMBERT, S ;

LAFFITTE, JA .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :555-567

[10] A NEW ENANTIOSELECTIVE SYNTHESIS OF GLYCIDATES VIA DYNAMIC KINETIC RESOLUTION OF RACEMIC 2-CHLORO-3-KETO ESTERS USING CHIRAL RU(II) COMPLEXES [J].

GENET, JP ;

DEANDRADE, MCC ;

RATOVELOMANANAVIDAL, V .

TETRAHEDRON LETTERS, 1995, 36 (12) :2063-2066

← 1 2 3 4 →