DYNAMIC KINETIC RESOLUTION UTILIZING A CHIRAL AUXILIARY BY STEREOSELECTIVE SN2 ALKYLATION WITH MALONIC ESTER ENOLATE

被引：18

作者：

KUBO, A ^{[1
]}

TAKAHASHI, M ^{[1
]}

KUBOTA, H ^{[1
]}

NUNAMI, KI ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 35期

关键词：

D O I：

10.1016/0040-4039(95)01236-B

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dynamic kinetic resolution by highly stereoselective carbon-carbon bond formation utilizing 2-oxoimidazolidine-4-carboxylate as a chiral auxiliary was exploited. The reaction of tert-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxoimidazolidine-4-carboxylate (1) with sodium dimethyl malonate in HMPA at room temperature predominantly afforded tert-butyl (4S)-1-methyl-3-((2R)-2-methyl-3,3-bis(methoxycarbonyl)propionyl)-2-oxoimidazolidine-4-carboxylate ((S,R)-2a) in a good yield.

引用

页码：6251 / 6252

页数：2

共 10 条

[1] 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

[2]

Kagan H. B., 1988, KINETIC RESOLUTION, V18, P249

[3] REACTION OF (R)-PANTOLACTONE ESTERS OF ALPHA-BROMOACIDS WITH AMINES - A REMARKABLE SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-AMINO ESTERS [J].

KOH, K ;

BEN, RN ;

DURST, T .

TETRAHEDRON LETTERS, 1993, 34 (28) :4473-4476

[4] STEREOSELECTIVE S(N)2 REACTIONS OF THE (R)-PANTOLACTONE ESTER OF RACEMIC ALPHA-HALO CARBOXYLIC-ACIDS WITH ARYLOXIDES - A SYNTHESIS OF (S)-2-ARYLOXY AND (S)-2-HYDROXY ACIDS [J].

KOH, K ;

DURST, T .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4683-4686

[5] 2-OXOIMIDAZOLIDINE-4-CARBOXYLATE AS A NOVEL CHIRAL AUXILIARY FOR KINETIC RESOLUTION [J].

KUBOTA, H ;

KUBO, A ;

NUNAMI, K .

TETRAHEDRON LETTERS, 1994, 35 (19) :3107-3110

[6] STEREOSELECTIVE HYDROGENATION VIA DYNAMIC KINETIC RESOLUTION [J].

NOYORI, R ;

IKEDA, T ;

OHKUMA, T ;

WIDHALM, M ;

KITAMURA, M ;

TAKAYA, H ;

AKUTAGAWA, S ;

SAYO, N ;

SAITO, T ;

TAKETOMI, T ;

KUMOBAYASHI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (25) :9134-9135

[7] DYNAMIC KINETIC RESOLUTION BY STEREOSPECIFIC AMINATION UTILIZING 2-OXOIMIDAZOLIDINE-4-CARBOXYLATE AS A NOVEL CHIRAL AUXILIARY [J].

NUNAMI, KI ;

KUBOTA, H ;

KUBO, A .

TETRAHEDRON LETTERS, 1994, 35 (46) :8639-8642

[8]

Rossi R., 1968, GAZZ CHIM ITAL, V98, P1391

[9] A NEW ROUTE TO HIGHLY ENANTIOMERICALLY ENRICHED (Z)-(1-METHYL-2-BUTENYL)BORONIC ESTERS [J].

STURMER, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (01) :59-60

[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

← 1 →