Preparation of desymmetrised meso-tartrate derivatives -: synthesis and utility of (R′,R′,R,S)-2,3-butane diacetal protected dimethyl tartrate

被引:32
作者
Dixon, DJ [1 ]
Foster, AC [1 ]
Ley, SV [1 ]
Reynolds, DJ [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 12期
关键词
D O I
10.1039/a902733e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 2,3-butane diacetal protected dimethyl tartrate (R',R',R,S)-1 using a chiral memory protocol and its utility for the preparation of desymmetrised meso-tartrate derivatives through selective transesterification and aminolysis of the spatially different carboxylate termini is described.
引用
收藏
页码:1631 / 1633
页数:3
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共 28 条
  • [21] Asymmetric desymmetrization of sigma-symmetrical diols: The role of chelation in the diastereoselective acetal cleavage induced by the chiral alpha-sulfinyl carbanion
    Maezaki, N
    Soejima, M
    Sakamoto, A
    Sakamoto, I
    Matsumori, Y
    Tanaka, T
    Ishida, T
    In, Y
    Iwata, C
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (01) : 29 - 32
  • [22] Butane 2,3-bisacetal protection of vicinal diequatorial diols
    Montchamp, JL
    Tian, F
    Hart, ME
    Frost, JW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3897 - 3899
  • [23] HIGHLY EFFICIENT ASYMMETRIC-SYNTHESIS OF (S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL FROM GLYCEROL
    MUKAIYAMA, T
    TANABE, Y
    SHIMIZU, M
    [J]. CHEMISTRY LETTERS, 1984, (03) : 401 - 404
  • [24] ASYMMETRIC ACYLATION OF MESO-1,2-DIOLS WITH D-KETOPINIC ACID CHLORIDE
    MUKAIYAMA, T
    TOMIOKA, I
    SHIMIZU, M
    [J]. CHEMISTRY LETTERS, 1984, (01) : 49 - 52
  • [25] OIYAMA AT, 1998, TETRAHEDRON LETT, V39, P397
  • [26] THE BIOCATALYTIC APPROACH TO THE PREPARATION OF ENANTIOMERICALLY PURE CHIRAL BUILDING-BLOCKS
    SANTANIELLO, E
    FERRABOSCHI, P
    GRISENTI, P
    MANZOCCHI, A
    [J]. CHEMICAL REVIEWS, 1992, 92 (05) : 1071 - 1140
  • [27] Enantioselective synthesis through enzymatic asymmetrization
    Schoffers, E
    Golebiowski, A
    Johnson, CR
    [J]. TETRAHEDRON, 1996, 52 (11) : 3769 - 3826
  • [28] LIPASE-SUPPORTED SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS
    THEIL, F
    [J]. CHEMICAL REVIEWS, 1995, 95 (06) : 2203 - 2227