A highly enantioselective synthesis of 5- (ι-menthyloxy) -4-substituted-3-chloro-2(5H) -furanones 被引量：1

A highly enantioselective synthesis of 5- (ι-menthyloxy) -4-substituted-3-chloro-2(5H) -furanones

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摘要 In this paper, stereocontrolled tandem Michael addition-elimination reaction of the novel chiral source, S-(ι-menthyloxy)-3,4-dichloro-2(5H)-furanone, with various thiols and amines has been investigated. A series of new enantiomerically pure compounds, 5-(ι-menthyloxy)-4-substituted-3-cnloro-2(5H)-furanones, were obtained in good yields with d. e.(?)98% under mild conditions. In this paper, stereocontrolled tandem Michael addition-elimination reaction of the novel chiral source, S-(ι-menthyloxy)-3,4-dichloro-2(5H)-furanone, with various thiols and amines has been investigated. A series of new enantiomerically pure compounds, 5-(ι-menthyloxy)-4-substituted-3-cnloro-2(5H)-furanones, were obtained in good yields with d. e.(?)98% under mild conditions.

作者耿哲黄彬陈庆华

机构地区 Department of Chemistry

出处《Chinese Journal of Chemistry》 SCIE CAS CSCD 1999年第2期189-195,共7页 中国化学（英文版）

基金 Project (No. 29132036) supported by the National Natural Science Foundation of China

关键词 Tandem Michael addition-elimination reaction 5-(ι-menthyloxy)-3 4-dichloro-2 (5H)-furanone enantiomerically pure compound 5-(ι-menthyloxy)-4-substituted-3-chloro-2(5H)-furanone Tandem Michael addition-elimination reaction, 5-(ι-menthyloxy)-3, 4-dichloro-2 (5H)-furanone, enantiomerically pure compound, 5-(ι-menthyloxy)-4-substituted-3-chloro-2(5H)-furanone

分类号 O621 [理学—有机化学]

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1郑绿茵,杨定乔,汪朝阳,李文辉,蒋启军.5-烷氧基-2(5H)-呋喃酮在有机合成中的应用[J].合成化学,2005,13(5):429-436.

1Qing Hua CHEN Bin HUANC Department of Chemistry,Beijing Normal University,Beijing 100875..A NOVEL CHIRAL 5-((-)-BORNYLOXY)-3,4-DICHLORO-2(5H)-FURANONE:THE EFFICIENT OPTICALLY PURE SYNTHESIS AND STEREOSPECIFIC TANDEM MICHAEL ADDITION-ELIMINATION REACTION[J].Chinese Chemical Letters,1993,4(8):675-678. 被引量：1
2范雪娥,黄敏,黄慧,陈庆华.An Efficient Synthesis of Highly Optically Active 4-Substituted- 2(5H)-furanones from Chiral 3-Bromo-2(5H)-furanone[J].Chinese Journal of Chemistry,2004,22(11):1359-1365.
3Geng, Z,Huang, B,Chen, QH.Crystal Structure of 5-(l-Menthyloxy)-3-Bromo-4-(R)-(+)-Methylbenzylamino-2(5H)-Furanone[J].Chinese Journal of Structural Chemistry,1999,18(2):32-34.
4Qing Hua CHEN Rei Qi SHU Department of Chemistry,Beijing Normal University,Beijing 100875.ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTION BY A CHIRAL SOURCE,5-(1-MENTHYLOXY)-2(5-H)-FURANONE[J].Chinese Chemical Letters,1990,1(1):45-46.
5Geng, Z,Chen, QH.Crystal Structure of 5-(l-Menthyloxy)-3-Chloro-4-Pyrolidinyl-2(5H)-Furanone[J].Chinese Journal of Structural Chemistry,1999,18(2):35-38. 被引量：1
6李鹏,赵刚,朱仕正.Highly Enantioselective Synthesis of a-Trifluoromethyldi- hydropyrans Using a Chiral Trifluoroethyl-substituted Thiourea Catalyst Derived from Amino Acid[J].Chinese Journal of Chemistry,2011,29(12):2749-2758.
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10孙文华,杨世琰,汪汉卿,周全福,郁开北.Heterometallic Trinuclear Carbonyl Sulfido Clusters and the Tetranuclear Intermediate via Electrophilic Addition-Elimination Reaction[J].Science China Chemistry,1994,37(12):1409-1420.

Chinese Journal of Chemistry

1999年第2期

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A highly enantioselective synthesis of 5- (ι-menthyloxy) -4-substituted-3-chloro-2(5H) -furanones 被引量：1

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