ON THE ASYMMETRIC DIHYDROXYLATION OF (2S,3R) 5-PHENYLPENT-4-EN-2,3-DIOL DERIVATIVES

被引：2
|
作者：
FRONZA, G
FUGANTI, C
GRASSELLI, P
MELE, A
机构：
[1] Dipartimento di Chimica del Politecnico, Centro CNR per lo Studio delle Sostanze Organiche Naturali
来源：
TETRAHEDRON | 1994年 / 50卷 / 17期
关键词：
D O I：
10.1016/S0040-4020(01)90413-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sharpless OsO4 asymmetric dihydroxylation of derivatives of the unsaturated (2S,3R) diols 2 affords products 7a,b and 10 and the diastereoisomers 8a,b and 11, respectively, in ratios depending upon the nature of the ligand (dihydroquinine and dihydroquinidine 4-chlorobenzoates), the mode of hydroxyl groups protection and the pattern of double bond substitution.
引用
收藏
页码：5021 / 5026
页数：6
相关论文
共 50 条
  • [1] Short asymmetric syntheses of sphinganine [(2S,3R)-2-aminooctadecane-1,3-diol] and its C(2)-epimer
    Pinto, Solange Da Silva
    Davies, Stephen G.
    Fletcher, Ai M.
    Newton, Sophie K.
    Roberts, Paul M.
    Thomson, James E.
    TETRAHEDRON LETTERS, 2021, 66
  • [2] ASYMMETRIC HYDROGENATION WITH 1,4-BIS(DIMETHYLAMINO)-(2S,3S)-BUTANE-2,3-DIOL(DBD)-LITHIUM AND 1,4-BIS(DIMETHYLAMINO)-(2R,3R)-BUTANE-2,3-DIOL(DBD)-LITHIUM ALUMINUM-HYDRIDE
    SEEBACH, D
    DAUM, H
    CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (05): : 1748 - 1763
  • [3] The asymmetric synthesis of (2S,3R)-capreomycidine
    DeMong, DE
    Williams, RM
    TETRAHEDRON LETTERS, 2001, 42 (21) : 3529 - 3532
  • [4] Asymmetric synthesis of (2S,3R,4R)-ethoxycarbonylcyclopropyl phosphonoglycine
    Hannour, S
    Roumestant, ML
    Viallefont, P
    Riche, C
    Martinez, J
    El Hallaoui, A
    Ouazzani, F
    TETRAHEDRON-ASYMMETRY, 1998, 9 (13) : 2329 - 2332
  • [5] A new asymmetric synthesis of (2S,3R,4R,5S)-trihydroxypipecolic acid
    Tsimilaza, Andriamihamina
    Tite, Tony
    Boutefnouchet, Sabrina
    Lallemand, Marie-Christine
    Tillequin, Francois
    Husson, Henri-Philippe
    TETRAHEDRON-ASYMMETRY, 2007, 18 (13) : 1585 - 1588
  • [6] Total synthesis of (+)-(2S,3R)-piscidic acid via catalytic asymmetric dihydroxylation of a trisubstituted olefin
    Toshima, H
    Saito, M
    Yoshihara, T
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1999, 63 (05) : 964 - 967
  • [7] Synthesis and α-mannosidase inhibitory evaluation of (2R,3R,4S)- and (2S,3R,4S)-2-(aminomethyl)pyrrolidine-3,4-diol derivatives
    Popowycz, F
    Gerber-Lemaire, S
    Rodriguez-García, E
    Schütz, C
    Vogel, P
    HELVETICA CHIMICA ACTA, 2003, 86 (06) : 1914 - 1948
  • [8] (3R,4S,5S)-4-hydroxy-3-methyl-5-[(2S,3R)-3-methylpent-4-en-2-yl] tetrahydrofuran-2-one
    Becker, Annika
    Schuermann, Markus
    Preut, Hans
    Hiersemann, Martin
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1517 - U2536
  • [9] (2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates
    Berg, C. Annette
    Eichenauer, Nils C.
    Pietruszka, Joerg
    PURE AND APPLIED CHEMISTRY, 2012, 84 (11) : 2339 - 2416
  • [10] Synthesis of (2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol
    Bischop, Martina
    Cmrecki, Vesna
    Ophoven, Vera
    Pietruszka, Joerg
    SYNTHESIS-STUTTGART, 2008, (15): : 2488 - 2490
12345