Enantio- and Diastereoselective Synthesis of syn-β-Hydroxyallylsilanes via a Chiral (Z)-γ-Silylailylboronate

被引:27
|
作者
Lira, Ricardo [1 ]
Roush, William R. [1 ]
机构
[1] Scripps Florida, Dept Chem, Jupiter, FL 33458 USA
关键词
D O I
10.1021/ol7018746
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
syn-beta-Hydroxyallylsilanes of general structure 11 and 28 are prepared in 50-86% yield and 91-95% ee (for aliphatic aldehydes; 50% ee for benzaldehyde) via the BF(3)center dot Et(2)O-promoted gamma-silylallylboration reactions, using reagents 14 and 15.
引用
收藏
页码:4315 / 4318
页数:4
相关论文
共 50 条
  • [1] Enantio- and Diastereoselective Synthesis of Chiral Syn-Aryl β-Hydroxy α-Amino Esters via Biocatalytic Dynamic Reductive Kinetic Resolution
    Zhang, Qing-Chun
    Lu, Zuo-Lin
    Hu, Chen
    Zhu, Kejie
    Jiang, Meifen
    Huang, Zedu
    Chen, Fener
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (07) : 1700 - 1703
  • [2] Enantio- and diastereoselective synthesis of erysulfone and erysulfoxide
    Bourdeau, L
    Sutherland, AG
    TETRAHEDRON LETTERS, 1997, 38 (52) : 9081 - 9084
  • [3] Role of Cinchona Alkaloids in the Enantio- and Diastereoselective Synthesis of Axially Chiral Compounds
    Portolani, Chiara
    Centonze, Giovanni
    Righi, Paolo
    Bencivenni, Giorgio
    ACCOUNTS OF CHEMICAL RESEARCH, 2022, : 3551 - 3571
  • [4] Enantio- and diastereoselective synthesis of γ-amino alcohols
    Verkade, Jorge M. M.
    Quaedflieg, Peter J. L. M.
    Verzijl, Gerard K. M.
    Lefort, Laurent
    van Delft, Floris L.
    de Vries, Johannes G.
    Rutjes, Floris P. J. T.
    CHEMICAL COMMUNICATIONS, 2015, 51 (77) : 14462 - 14464
  • [5] Organocatalytic enantio- and diastereoselective cycloetherification via dynamic kinetic resolution of chiral cyanohydrins
    Naoki Yoneda
    Yuki Fujii
    Akira Matsumoto
    Keisuke Asano
    Seijiro Matsubara
    Nature Communications, 8
  • [6] Organocatalytic enantio- and diastereoselective cycloetherification via dynamic kinetic resolution of chiral cyanohydrins
    Yoneda, Naoki
    Fujii, Yuki
    Matsumoto, Akira
    Asano, Keisuke
    Matsubara, Seijiro
    NATURE COMMUNICATIONS, 2017, 8
  • [7] Organocatalytic Enantio- and Diastereoselective Cycloetherification via Dynamic Kinetic Resolution of Chiral Cyanohydrins
    Yoneda, Naoki
    Fuji, Yuki
    Matsumoto, Akira
    Asano, Keisuke
    Matsubara, Seijiro
    SYNTHESIS-STUTTGART, 2018, 50 (05): : A33 - A35
  • [8] Organocatalytic Enantio- and Diastereoselective Cycloetherification via Dynamic Kinetic Resolution of Chiral Cyanohydrins
    Yoneda, N.
    Fuji, Y.
    Matsumoto, A.
    Asano, K.
    Matsubara, S.
    SYNLETT, 2018, 29 (04) : A33 - A35
  • [9] Enantio- and Diastereoselective Spiroketalization Catalyzed by Chiral Iridium Complex
    Hamilton, James Y.
    Roessler, Simon L.
    Carreira, Erick M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (24) : 8082 - 8085
  • [10] Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-alkenyl carboxamides via reductive aldol reactions of morpholine 4-methyl-2,3-pentadienoic carboxamide with diisopinocampheylborane
    El Hilali, Xochina
    Roush, William R.
    TETRAHEDRON LETTERS, 2015, 56 (23) : 3281 - 3284