Aziridine-mediated asymmetric synthesis of quaternary β-amino acids using 2H-azirine 2-carboxylate esters

被引：49

作者：

Davis, FA ^{[1
]}

Deng, JH

Zhang, YL

Haltiwanger, RC

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

[2] GlaxoSmithKline, King Of Prussia, PA 19406 USA

来源：

TETRAHEDRON | 2002年 / 58卷 / 35期

基金：

美国国家卫生研究院;

关键词：

asymmetric synthesis; aziridines; beta-amino acids; N-sulfinyl imines;

D O I：

10.1016/S0040-4020(02)00727-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective hydrogenation of enantiopure 3-substituted and 3,3-disubstituted aziridine 2-carboxylate esters affords beta-amino acids and quaternary beta-amino acids, respectively, in good yield. The aziridines are prepared via an aza-Darzens reaction of alpha-bromoenolates with enantiopure sulfinimines (N-sulfinyl imines) and by addition of Grignard reagents to 2H-azirine 2-carboxylate esters. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7135 / 7143

页数：9

相关论文

共 41 条

[11] Asymmetric synthesis of quaternary α-amino phosphonates using sulfinimines [J].

Davis, FA ;

Lee, S ;

Yan, HX ;

Titus, DD .

ORGANIC LETTERS, 2001, 3 (11) :1757-1760

[12] Asymmetric synthesis of beta-substituted alpha-amino acids using 2H-azirine-2-carboxylate esters. Synthesis of 3,3-disubstituted aziridine-2-carboxylate esters [J].

Davis, FA ;

Liang, CH ;

Liu, H .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3796-3797

[13] ASYMMETRIC-SYNTHESIS AND REACTIONS OF CIS-N-(P-TOLUENESULFINYL)AZIRIDINE-2-CARBOXYLIC ACIDS [J].

DAVIS, FA ;

ZHOU, P ;

REDDY, GV .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3243-3245

[14] Improved synthesis of enantiopure sulfinimines (thiooxime S-oxides) from p-toluenesulfinamide and aldehydes and ketones [J].

Davis, FA ;

Zhang, YL ;

Andemichael, Y ;

Fang, TA ;

Fanelli, DL ;

Zhang, HM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1403-1406

[15] 2-methyl N-(p-toluenesulfinyl)aziridine-2-carboxylic acid: Asymmetric synthesis of alpha-methylphenylalanine and alpha-methyl-beta-phenylserine [J].

Davis, FA ;

Liu, H ;

Reddy, GV .

TETRAHEDRON LETTERS, 1996, 37 (31) :5473-5476

[16]

Davis FA, 1998, CHEM SOC REV, V27, P13

[17] Applications of the sulfinimine-mediated asymmetric strecker synthesis to the synthesis of α-alkyl α-amino acids [J].

Davis, FA ;

Lee, S ;

Zhang, HM ;

Fanelli, DL .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8704-8708

[18]

DREY CNC, 1985, CHEM BIOCH AMINO ACI, pCH3

[19] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].

Enders, D ;

Reinhold, U .

TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946

[20] BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS [J].

EVANS, DA ;

FAUL, MM ;

BILODEAU, MT ;

ANDERSON, BA ;

BARNES, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5328-5329

← 1 2 3 4 5 →