DIOLS AS SUBSTRATES IN LIPASE-CATALYZED ENANTIOSELECTIVE ACYLATIONS - A BRIEF REVIEW

被引:29
作者
THEIL, F
机构
[1] Institut für Angewandte Chemie Berlin-Adlershof, D-12484 Berlin
关键词
D O I
10.1016/0920-5861(94)80121-5
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An overview on lipase-catalyzed enantioselective acylations of diols in organic solvents is presented. The application of this biocatalytic process on diols as a special type of bifunctional compounds as substrates is directed on the synthesis of enantiomerically pure building blocks. Prochiral acyclic and cyclic diols can be successfully made asymmetric by using different types of lipases and acylating agents. The kinetic resolution of racemic cyclic and acyclic diols is demonstrated by various examples.
引用
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页码:517 / 536
页数:20
相关论文
共 110 条
  • [1] ENZYMATIC ESTER HYDROLYSIS AND SYNTHESIS - 2 APPROACHES TO CYCLOALKANE DERIVATIVES OF HIGH ENANTIOMERIC PURITY
    ADER, U
    BREITGOFF, D
    KLEIN, P
    LAUMEN, KE
    SCHNEIDER, MP
    [J]. TETRAHEDRON LETTERS, 1989, 30 (14) : 1793 - 1796
  • [2] TOTAL SYNTHESIS OF (-)-OUDEMANSIN-X BASED ON ENZYMATIC RESOLUTION USING IMMOBILIZED LIPASE
    AKITA, H
    UMEZAWA, I
    NOZAWA, M
    NAGUMO, S
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (05) : 757 - 760
  • [3] TANDEM CYCLOADDITION-ENZYMATIC TRANSESTERIFICATION - AN ENANTIOSELECTIVE DIELS-ALDER REACTION EQUIVALENT
    ANDREU, C
    MARCO, JA
    ASENSIO, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11): : 3209 - 3210
  • [4] AN EFFICIENT ENANTIOSELECTIVE PREPARATION OF 2-SUBSTITUTED-3-HYDROXYPROPIONIC ACIDS VIA CHEMOENZYMATIC REACTION
    ATSUUMI, S
    NAKANO, M
    KOIKE, Y
    TANAKA, S
    OHKUBO, M
    YONEZAWA, T
    FUNABASHI, H
    HASHIMOTO, J
    MORISHIMA, H
    [J]. TETRAHEDRON LETTERS, 1990, 31 (11) : 1601 - 1604
  • [5] ACID-CATALYZED RACEMIZATION OF 1-(HETEROCYCLYLOXY)-2,3-PROPANEDIOLS
    BARLOW, JJ
    BLOCK, MH
    HUDSON, JA
    LEACH, A
    LONGRIDGE, JL
    MAIN, BG
    NICHOLSON, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) : 5158 - 5162
  • [6] ASYMMETRIC-SYNTHESIS AND ABSOLUTE-CONFIGURATION OF 5,10-DIDEAZA-5,6,7,8-TETRAHYDROPTEROIC ACID AND 5,10-DIDEAZA-5,6,7,8-TETRAHYDROFOLIC ACID (DDATHF)
    BARNETT, CJ
    WILSON, TM
    [J]. TETRAHEDRON LETTERS, 1989, 30 (46) : 6291 - 6294
  • [7] THE ENANTIOMERS OF 1-BETA-ADENYL-2-ALPHA-HYDROXY-3-BETA-HYDROXYMETHYL-CYCLOBUTANE
    BASCHANG, G
    INDERBITZIN, W
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (02) : 193 - 196
  • [8] Bestmann H. J., 1991, ANGEW CHEM, V103, P78
  • [9] BESTMANN HJ, 1991, ANGEW CHEM INT EDIT, V90, P86
  • [10] ENZYMATIC RESOLUTION OF 1,2-DIOLS - PREPARATION OF OPTICALLY PURE DROPROPIZINE
    BIANCHI, D
    BOSETTI, A
    CESTI, P
    GOLINI, P
    [J]. TETRAHEDRON LETTERS, 1992, 33 (22) : 3231 - 3234