Asymmetric hydrolysis of pro-chiral 3,3-disubstituted 2,4-diacetoxycyclohexa-1,4-dienes

被引:15
|
作者
Renouf, P
Poirier, JM
Duhamel, P
机构
[1] UNIV ROUEN,FAC SCI,CNRS,URA 464,F-76821 MONT ST AIGNAN,FRANCE
[2] UNIV ROUEN,IRCOF,F-76821 MONT ST AIGNAN,FRANCE
关键词
D O I
10.1039/a606001c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric enzymatic hydrolysis of pro-chiral 3,3-disubstituted 2,4-diacetoxycyclohexa-1,4-dienes 2 affords in high yields optically pure 2,2-disubstituted 3-acetoxycyclohex-3-enones 1 (>98% ee). Under mild conditions Candida cylindracea lipase (enzyme/substrate ratio = 2%) hydrolyses specifically the pro-S enol ester function of the pro-chiral starting material 2.
引用
收藏
页码:1739 / 1745
页数:7
相关论文
共 45 条
  • [31] Methylation ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of Briaran diterpenes
    Balasubramaniam, RP
    Moss, DK
    Wyatt, JK
    Spence, JD
    Gee, A
    Nantz, MH
    TETRAHEDRON, 1997, 53 (22) : 7429 - 7444
  • [32] Organocatalyzed nucleophilic addition of pyrazoles to 2H-azirines: asymmetric synthesis of 3,3-disubstituted aziridines and kinetic resolution of racemic 2H-azirines
    An, Dong
    Guan, Xukai
    Guan, Rui
    Jin, Lajiao
    Zhang, Guangliang
    Zhang, Suoqin
    CHEMICAL COMMUNICATIONS, 2016, 52 (75) : 11211 - 11214
  • [33] SYNTHESES OF 1,3-CYCLOPENTANEDIONES VIA INTRA-MOLECULAR OXIDATIVE COUPLING OF 3,3-DISUBSTITUTED 2,4-PENTANEDIONES BY MEANS OF CU(OTF)2
    KOBAYASHI, Y
    TAGUCHI, T
    MORIKAWA, T
    TETRAHEDRON LETTERS, 1978, (38) : 3555 - 3556
  • [34] Design, Synthesis and Use of Novel 3,3′-Disubstituted 2,2′-Bipyridine-Based Chiral Ligands: Asymmetric Catalysis in Direct Aldol Reactions
    Zhao, Hong-Wu
    Li, Hai-Long
    Yue, Yuan-Yuan
    Qin, Xiao
    Sheng, Zhi-Hui
    Cui, Jin
    Su, Shi
    Song, Xiu-Qing
    Yan, Hong
    Zhong, Ru-Gang
    SYNLETT, 2012, (13) : 1990 - 1994
  • [35] ASYMMETRIC BAYLIS-HILLMAN REACTIONS USING CHIRAL 2,3-DISUBSTITUTED 1,4-DIAZABICYCLO[2.2.2]OCTANES CATALYSTS UNDER HIGH-PRESSURE CONDITIONS
    OISHI, T
    OGURI, H
    HIRAMA, M
    TETRAHEDRON-ASYMMETRY, 1995, 6 (06) : 1241 - 1244
  • [36] On the way to α-methyl-α-amino acids;: Unusual elimination-addition in 3,3-disubstituted 1,4-benzodiazepin-2-ones and inversion of enantioselectivity in the lipase catalyzed acetylation
    Avdagic, A
    Sunjic, V
    CROATICA CHEMICA ACTA, 2000, 73 (03) : 743 - 753
  • [37] Asymmetric synthesis of beta-substituted alpha-amino acids using 2H-azirine-2-carboxylate esters. Synthesis of 3,3-disubstituted aziridine-2-carboxylate esters
    Davis, FA
    Liang, CH
    Liu, H
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12): : 3796 - 3797
  • [38] Design and preparation of 3,3′-disubstituted 2,2′-bis(oxazolyl)-1,1′-binaphthyls (boxax):: New chiral bis(oxazoline) ligands for catalytic asymmetric Wacker-type cyclization
    Uozumi, Y
    Kyota, H
    Kato, K
    Ogasawara, M
    Hayashi, T
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05): : 1620 - 1625
  • [39] ASYMMETRIC-SYNTHESIS OF 2,4-DISUBSTITUTED BUTYROLACTONES USING THE IRON CHIRAL AUXILIARY [ETA-5-C5H5)FE(CO)(PPH3)]
    DAVIES, SG
    POLYWKA, R
    WARNER, P
    TETRAHEDRON, 1990, 46 (13-14) : 4847 - 4856