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
  • [31] An enantio- and diastereoselective synthesis of (-)-isoretronecanol and (+)-trachelanthamidine from a meso precursor
    Konno, H
    Kishi, M
    Hiroya, K
    Ogasawara, K
    HETEROCYCLES, 1998, 49 : 33 - 37
  • [32] Merging chiral organocatalysts: enantio- and diastereoselective direct vinylogous Mannich reaction of alkylimines
    Xiong, Xiao-Feng
    Jia, Zhi-Jun
    Du, Wei
    Jiang, Kun
    Liu, Tian-Yu
    Chen, Ying-Chun
    CHEMICAL COMMUNICATIONS, 2009, (45) : 6994 - 6996
  • [33] Enantio- and Diastereoselective Cyclopropanation of β,γ-Unsaturated α-Ketoester by a Chiral Phosphate/Indium(III) Complex
    Zhong, Xingren
    Lv, Jian
    Luo, Sanzhong
    ORGANIC LETTERS, 2017, 19 (12) : 3331 - 3334
  • [34] Enantio- or diastereoselective oxidation of (methylthio)methylphosphonates as a route to precursors of chiral sulfoxides.
    Cardellicchio, C
    Fracchiolla, G
    Naso, F
    Tortorella, P
    TETRAHEDRON, 1999, 55 (02) : 525 - 532
  • [35] Enantio- and Diastereoselective Variations on α-Iminonitriles: Harnessing Chiral Cyclopropenimine-Thiourea Organocatalysts
    Lee, Hooseung
    Nam, Hyeongwoo
    Lee, Sarah Yunmi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (05) : 3065 - 3074
  • [36] A practical synthesis of syn- and anti-α,β-dihydroxyphosphinates via diastereoselective reduction of α-phosphinoyl ketones
    Rojas-Cabrera, Haydee
    Hernandez-Perez, Julio M.
    Ho, Minhhuy
    Hernandez-Fernandez, Eugenio
    Ordonez, Mario
    TETRAHEDRON-ASYMMETRY, 2008, 19 (02) : 161 - +
  • [37] Enantio- and diastereoselective synthesis of spiropyrazolones via an organocatalytic [1+2+3] multicomponent reaction
    Ji, Yan-Ling
    Li, He-Ping
    Ai, Yue-Yan
    Li, Guo
    He, Xiang-Hong
    Huang, Wei
    Huang, Rui-Zhen
    Han, Bo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (41) : 9217 - 9225
  • [38] Enantio- and Diastereoselective Synthesis of syn-β-Hydroxy-α-vinyl Carboxylic Esters via Reductive Aldol Reactions of Ethyl Allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT Analysis of the Hydroboration Pathway
    Kister, Jeremy
    Ess, Daniel H.
    Roush, William R.
    ORGANIC LETTERS, 2013, 15 (21) : 5436 - 5439
  • [39] Organocatalytic enantio- and diastereoselective synthesis of highly substituted δ-lactones via a Michael-cyclization cascade
    Agrawal, Santosh
    Molleti, Nagaraju
    Singh, Vinod K.
    CHEMICAL COMMUNICATIONS, 2015, 51 (48) : 9793 - 9796
  • [40] Enantio- and Diastereoselective Synthesis of (E)-1,5-syn-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin
    Kister, Jeremy
    Nuhant, Philippe
    Lira, Ricardo
    Sorg, Achim
    Roush, William R.
    ORGANIC LETTERS, 2011, 13 (07) : 1868 - 1871