Regio- and Enantioselective Monoborylation of Alkenylsilanes Catalyzed by an Electron-Donating Chiral Phosphine-Copper(I) Complex

被引：38
|
作者：
Kubota, Koji [1 ]
Yamamoto, Eiji [1 ]
Ito, Hajime [1 ]
机构：
[1] Hokkaido Univ, Div Chem Proc Engn, Fac Engn, Sapporo, Hokkaido 0608628, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 18期
基金：
日本学术振兴会;
关键词：
asymmetric catalysis; borylation; copper; silanes; synthetic methods; ALLYLIC CARBONATES; ALPHA; BETA-UNSATURATED ESTERS; COPPER(I)-CATALYZED REACTION; ASYMMETRIC-SYNTHESIS; BORYL SUBSTITUTION; EFFICIENT ROUTE; BETA-BORATION; HYDROBORATION; DIBORON; ADDITIONS;
D O I：
10.1002/adsc.201300765
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An asymmetric monoborylation of alkenylsilanes catalyzed by a copper(I) complex with the chiral bisphosphine ligand BenzP* is reported. The reaction proceeded with excellent regioselectivity and high enantioselectivity to afford the corresponding optically active organoboronate esters with a stereogenic CB bond containing a vicinal silyl group. The synthetic utility of the product is demonstrated through stepwise transformations to multifunctional optically active compounds in a stereospecific manner.
引用
收藏
页码：3527 / 3531
页数：5
相关论文
共 15 条
  • [1] Copper-Catalyzed Regio- and Enantioselective Synthesis of Chiral Enol Acetates and β-Substituted Aldehydes
    Fananas-Mastral, Martin
    Feringa, Ben L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) : 13152 - 13153
  • [2] Chiral phosphine-catalyzed regio- and enantioselective allylic amination of Morita-Baylis-Hillman acetates
    Ma, Guang-Ning
    Cao, Shu-Hua
    Shi, Min
    TETRAHEDRON-ASYMMETRY, 2009, 20 (09) : 1086 - 1092
  • [3] Regio- and Enantioselective Allylation of Indole Catalyzed by a Planar-chiral Cyclopentadienyl-Ruthenium Complex
    Onitsuka, Kiyotaka
    Kameyama, Chiaki
    Sasai, Hiroaki
    CHEMISTRY LETTERS, 2009, 38 (05) : 444 - 445
  • [4] Regio- and Enantioselective Copper(I)-Catalyzed Hydroboration of Borylalkenes: Asymmetric Synthesis of 1,1-Diborylalkanes
    Feng, Xinhui
    Jeon, Heekyung
    Yun, Jaesook
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) : 3989 - 3992
  • [5] Regio- and enantioselective O-allylation of phenol and alcohol catalyzed by a planar-chiral cyclopentadienyl ruthenium complex
    Onitsuka, Kiyotaka
    Okuda, Haruki
    Sasai, Hiroaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) : 1454 - 1457
  • [6] Synthesis of chiral oxime ethers based on regio- and enantioselective allylic substitution catalyzed by iridium-pybox complex
    Miyabe, Hideto
    Matsumura, Akira
    Yoshida, Kazumasa
    Takemoto, Yoshiji
    TETRAHEDRON, 2009, 65 (23) : 4464 - 4470
  • [7] Nickel/Bronsted acid dual-catalyzed regio- and enantioselective hydrophosphinylation of 1,3-dienes: access to chiral allylic phosphine oxides
    Long, Jiao
    Li, Yuqiang
    Zhao, Weining
    Yin, Guoyin
    CHEMICAL SCIENCE, 2022, 13 (05) : 1390 - 1397
  • [8] Highly Regio- and Enantioselective Nitroso Diels-Alder Reaction of 1,3-Diene-1-carbamates Catalyzed by Chiral N,N′-Dioxide/Copper(II) Complex
    Lu, Yan
    Zhou, Yuhang
    Zhang, Jingchuan
    Lin, Lili
    Liu, Xiaohua
    Feng, Xiaoming
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (01) : 186 - 191
  • [9] Chiral Gold Complex Catalyzed Cycloisomerization/Regio- and Enantioselective Nitroso-Diels-Alder Reaction of 1,6-Diyne Esters with Nitrosobenzenes
    Yu, Lei
    Li, Wenhai
    Tapdara, Anyawan
    Kyne, Sara Helen
    Harode, Mandeep
    Babaahmadi, Rasool
    Ariafard, Alireza
    Chan, Philip Wai Hong
    ACS CATALYSIS, 2022, 12 (12) : 7288 - 7299
  • [10] Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones
    Wang, De
    Wang, Guo-Peng
    Sun, Yao-Liang
    Zhu, Shou-Fei
    Wei, Yin
    Zhou, Qi-Lin
    Shi, Min
    CHEMICAL SCIENCE, 2015, 6 (12) : 7319 - 7325
12