Tandem hydroboration/reduction of trisubstituted β,γ-unsaturated esters for the asymmetric synthesis of chiral 1,3-diols

被引：7
作者：
Fordred, Paul S. [1 ]
Bull, Steven D. [1 ]
机构：
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 01期
基金：
英国工程与自然科学研究理事会;
关键词：
Hydroboration; Reduction; beta; gamma-Unsaturated ester; Chiral 1,3-diol; IpcBH(2); HYDROBORATING AGENT; ENANTIOMERIC PURITY; NMR ANALYSIS; MONOISOPINOCAMPHEYLBORANE; REDUCTION; ALKENES; OLEFINS; KETONES; DIOLS;
D O I：
10.1016/j.tetlet.2012.10.047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of a range of trisubstituted beta,gamma-unsaturated esters with 2 equiv of (-)-monoisopinocampheylborane results in hydroboration of their alkene functionalities and reduction of their ester groups to afford chiral 1,3-diols containing two new vicinal beta,gamma-(anti)-stereocentres in 67-85% enantiomeric excess. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：27 / 31
页数：5
相关论文
共 50 条
  • [41] Synthesis of 2-Keto-anti-1,3-diols by Chemoselective Tandem Oxidation of 2-B(pin)-Substituted Allylic Alcohols
    Hussain, Mahmud M.
    Toribio, Jorge Hernandez
    Carroll, Patrick J.
    Walsh, Patrick J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) : 6337 - 6340
  • [42] A one-pot diastereoselective synthesis of 1,3-diols and 1,3,5-triols via cascade reactions of arylalkynyl Grignard reagents with enol esters
    Jiao, Yinchun
    Zhao, Wenjing
    Deng, Shuang
    Tang, Zilong
    Liu, Wanqiang
    Wan, Yichao
    Zhong, Fuqi
    JOURNAL OF CHEMICAL RESEARCH, 2020, 44 (5-6) : 255 - 266
  • [43] Enantio- and diastereoselective synthesis of (protected) 2-formyl- and 2-(hydroxymethyl)-1-phenylalkane-1,3-diols from chiral 2-methoxy-3-tosyl-1,3-oxazolidines by subsequent asymmetric formylation and aldolization
    Steif, F
    Wibbeling, B
    Meyer, O
    Hoppe, D
    SYNTHESIS-STUTTGART, 2000, (05): : 743 - 753
  • [44] Recent Advances in Catalytic Asymmetric Synthesis of Chiral 1,2-Bis(boronic) Esters
    Ji Chonglei
    Gao Dewei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (05) : 1385 - 1402
  • [45] Stereoarrayed CF3-Substituted 1,3-Diols by Dynamic Kinetic Resolution: Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation
    Cotman, Andrej Emanuel
    Cahard, Dominique
    Mohar, Barbara
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (17) : 5294 - 5298
  • [46] Chiral ferrocenyl phosphine-phosphoramidite ligands for Cu-catalyzed asymmetric conjugate reduction of α,β-unsaturated esters
    Hou, Chuan-Jin
    Guo, Wei-Lei
    Hu, Xiang-Ping
    Deng, Jun
    Zheng, Zhuo
    TETRAHEDRON-ASYMMETRY, 2011, 22 (02) : 195 - 199
  • [47] One-pot and sequential asymmetric hydrogenation of β,δ-diketoesters into functionalized 1,3-diols:: From anti- to syn-stereoselectivity
    Blandin, V
    Carpentier, JF
    Mortreux, A
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (12) : 3421 - 3427
  • [48] Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations
    Medina, Casey
    Carter, Kyle P.
    Miller, Michael
    Clark, Timothy B.
    O'Neil, Gregory W.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18) : 9093 - 9101
  • [49] Stereoselective synthesis of syn,syn-2-methyl-1,3-diols through one-pot aldol-reduction sequence
    Galobardes, M
    Mena, M
    Romea, P
    Urpí, F
    Vilarrasa, J
    TETRAHEDRON LETTERS, 2002, 43 (35) : 6145 - 6148
  • [50] A highly diastereoselective TiCl4-mediated reduction of β-hydroxy ketones with BH3•py -: A very efficient and general synthesis of syn-1,3-diols
    Bartoli, G
    Bosco, M
    Marcantoni, E
    Massaccesi, M
    Rinaldi, S
    Sambri, L
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (24) : 4679 - 4684
12345