SYNTHESIS OF ENANTIOMERICALLY PURE 5-(L-MENTHYLOXY)-3,4-DIBROMO-2(5H)-FURANONE AND ITS TANDEM ASYMMETRIC MICHAEL ADDITION-ELIMINATION REACTION

被引:0
|
作者
CHEN, QH
GENG, Z
HUANG, B
机构
关键词
D O I
暂无
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The novel chiral 5-(l-menthyloxy)-3,4-dibromo-2(5H)-furanone 4b was prepared in enantiomerically pure form, and ifs tandem Michael addition-elimination reaction provide the corresponding new chiral sources 6a-6d or 7a-7e, respectively in good yield with de>98%.
引用
收藏
页码:401 / 404
页数:4
相关论文
共 38 条
  • [31] SYNTHESIS OF 3-HYDROXY-4,5-DIMETHYL-2(5H)-FURANONE AND ITS ANALOGS - UTILIZATION OF AN INTRAMOLECULAR DARZENS REACTION
    FRATER, G
    MULLER, U
    TETRAHEDRON LETTERS, 1993, 34 (17) : 2753 - 2756
  • [32] Synthesis and Crystal Structure of N,N′-Bis-[3-chloro-5-S-(l-menthyloxy)-2(5H)-4-furanon-yl]-propane-1,3-diamine
    宋秀美
    汪朝阳
    莫阳青
    毛郑州
    Chinese Journal of Structural Chemistry, 2009, 28 (05) : 537 - 540
  • [33] The stereoselective C-alkylation of chiral nitronic acid (4S*, 5R)-(+)-4-(6-nitro-6-carbethoxymethyl)-5-[(1R)-menthyloxy]-3,4-dihydro-2(5H)-furanone
    Zhang, Lei Lei
    Feng, Zhi Qiang
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2014, 91 (07) : 1335 - 1339
  • [34] Highly enantioselective synthesis of chiral 3,4-dihydro-2H-pyran-5-carbonitrile via tandem Michael addition/asymmetric transfer hydrogenation/cyclization reactions catalyzed by a bifunctional NoyoriIkariya type catalyst
    Zheng, Dongsong
    Liu, Rui
    Wang, Yu
    Cheng, Tanyu
    Liu, Guohua
    MOLECULAR CATALYSIS, 2018, 455 : 103 - 107
  • [35] A 3,4-dihalo-2(5H)-furanone initiated ring-opening reaction of DABCO in the absence of a metal catalyst and additive and its application in a one-pot two-step reaction
    Wu, Han-Qing
    Yang, Kai
    Chen, Xiao-Yun
    Arulkumar, Mani
    Wang, Neng
    Chen, Si-Hong
    Wang, Zhao-Yang
    GREEN CHEMISTRY, 2019, 21 (14) : 3782 - 3788
  • [36] Synthesis and characterization of chiral nitronic esters via O-alkylation of (4S*,5R)-(+)-4-(1'-nitro-1'-carbethoxymethyl)-5-[(1R)-menthyloxy]-3,4-dihydro-2(5H)-furanoae with alkyl halides
    Kang, FA
    Yin, CL
    She, SW
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16): : 5523 - 5527
  • [37] MICHAEL ADDITION OF BENZOYLACETONITRILE TO CHIRAL ALPHA-CYANOACRYLATES DERIVED FROM ENANTIOMERICALLY PURE ALPHA-HYDROXYALDEHYDES - SYNTHESIS OF 3-ALKOXYCARBONYL-4-ALKYL-2-AMINO-5-CYANO-6-PHENYL-4H-PYRAN
    JIMENEZ, B
    MARTIN, N
    MARTINEZGRAU, A
    SEOANE, C
    MARCO, JL
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (04) : 1381 - 1384
  • [38] OPTICALLY-ACTIVE TRANSITION-METAL COMPLEXES .104. ASYMMETRIC MICHAEL REACTIONS OF (RFE)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH=CH2] AND (SFE)-[ETA(5)-C5H5)FE(CO)(PPH3)COCH=CH2] - SYNTHESIS OF AN ENANTIOMERICALLY PURE PRECURSOR FOR VERAPAMIL - X-RAY CRYSTAL-STRUCTURE OF (RFERC)-((ETA-C5H5)FE(CO)(PPH3)COCH2CH2C(CN)(IPR)-[3,4-C6H3(OME)2])
    BRUNNER, H
    FORSTER, S
    NUBER, B
    ORGANOMETALLICS, 1993, 12 (10) : 3819 - 3827