2-OXOIMIDAZOLIDINE-4-CARBOXYLATE AS A NOVEL CHIRAL AUXILIARY FOR KINETIC RESOLUTION

被引：15

作者：

KUBOTA, H ^{[1
]}

KUBO, A ^{[1
]}

NUNAMI, K ^{[1
]}

机构：

[1] TANABE SEIYAKU CO LTD,APPL BIOCHEM RES LAB,YODOGAWA KU,OSAKA 532,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(00)76842-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A kinetic resolution by stereospecific amination using 2-oxoimidazolidine-4-carboxylate as a novel chiral auxiliary was investigated. The reaction of tert-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxoimidazolidine-4-carboxylate (5) with an equimolar benzylamine in CH2Cl2 proceeded stereospecifically to afford tert-butyl (4S)-1-methyl-3-((2R)-2-benzylaminopropionyl)-2-oxoimidazolidine-4-carboxylate ((S,R)-4) in a good yield, while (S,R)-5 was recovered quantitatively.

引用

页码：3107 / 3110

页数：4

共 10 条

[1] GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].

CHEN, CS ;

SIH, CJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06) :695-707

[2] SELECTIVE RING-OPENING REACTION OF STYRENE OXIDE WITH LITHIUM AZIDE IN THE PRESENCE OF CYCLODEXTRINS IN AQUEOUS-MEDIA [J].

GUY, A ;

DOUSSOT, J ;

GARREAU, R ;

GODEFROYFALGUIERES, A .

TETRAHEDRON-ASYMMETRY, 1992, 3 (02) :247-250

[3] STUDIES ON ANGIOTENSIN CONVERTING ENZYME-INHIBITORS .4. SYNTHESIS AND ANGIOTENSIN CONVERTING ENZYME INHIBITORY ACTIVITIES OF 3-ACYL-1-ALKYL-2-OXOIMIDAZOLIDINE-4-CARBOXYLIC ACID-DERIVATIVES [J].

HAYASHI, K ;

NUNAMI, K ;

KATO, J ;

YONEDA, N ;

KUBO, M ;

OCHIAI, T ;

ISHIDA, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (02) :289-297

[4] KINETIC RESOLUTION OF RACEMIC ALDEHYDES BY ENANTIOSELECTIVE ALKYLATION [J].

HAYASHI, M ;

MIWATA, H ;

OGUNI, N .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05) :1167-1171

[5]

Kagan H. B., 1988, TOP STEREOCHEM, V18, P249

[6]

KUBOTA H, 1992, CHEM PHARM BULL, V40, P1619

[7]

KUBOTA H, 1991, CHEM PHARM BULL, V39, P1374

[8]

SHIMIZU R, 1993, PEPTIDE CHEMISTRY 1992, P227

[9] COMMENTS ON THE PUTATIVE STEREOSELECTIVITY IN CYSTEINE-ALDEHYDE REACTIONS - SELECTIVE C(2) INVERSION AND C(4) EPIMERIZATION IN THIAZOLIDINE-4-CARBOXYLIC ACIDS [J].

SZILAGYI, L ;

GYORGYDEAK, Z .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (02) :427-432

[10] KINETIC RESOLUTION OF RACEMIC OLEFINS VIA ASYMMETRIC DIHYDROXYLATION [J].

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (17) :7864-7865

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