Asymmetric Synthesis of Trisubstituted Allenes: Copper-Catalyzed Alkylation and Arylation of Propargylic Phosphates

被引：90
|
作者：
Uehling, Mycah R. [1 ]
Marionni, Samuel T. [1 ]
Lalic, Gojko [1 ]
机构：
[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 01期
关键词：
AXIALLY CHIRAL ALLENYLSILANES; ARYLBORONIC ACIDS; STEREOSPECIFIC SYNTHESIS; ENANTIOENRICHED ALLENES; GOLDEN OPPORTUNITIES; COUPLING REACTION; ALCOHOLS; ESTERS; CARBOXYLATION; REARRANGEMENT;
D O I：
10.1021/ol2031119
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric synthesis of trisubstituted allenes is accomplished by copper-catalyzed alkylation and arylation of propargylic phosphates using organoboron nucleophiles. Excellent chirality transfer and regioselectivity, together with good functional group compatibility, were observed in reactions with both alkyl boranes and arylboronic esters.
引用
收藏
页码：362 / 365
页数：4
相关论文
共 50 条
  • [31] Enyne Chlorides: Substrates for Copper-Catalyzed Asymmetric Allylic Alkylation
    Li, Hailing
    Alexakis, Alexandre
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 1055 - 1058
  • [32] Enantioselective copper-catalyzed propargylic amination
    Detz, Remko J.
    Delville, Marielle M. E.
    Hiemstra, Henk
    van Maarseveen, Jan H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) : 3777 - 3780
  • [33] Synthesis of ( S )-Nyasol through a Copper-Catalyzed Propargylic Substitution
    Kobayashi, Yuichi
    Hirotsu, Takayuki
    [J]. SYNLETT, 2023, 34 (02) : 159 - 162
  • [34] Copper-Catalyzed Hydroamination of Terminal Allenes
    Blieck, Remi
    Bahri, Janet
    Taillefer, Marc
    Monnier, Florian
    [J]. ORGANIC LETTERS, 2016, 18 (06) : 1482 - 1485
  • [35] Synthesis and structure of intermediates in copper-catalyzed alkylation of diphenylphosphine
    Cain, Matthew F.
    Hughes, Russell P.
    Glueck, David S.
    Golen, James A.
    Moore, Curtis E.
    Rheingold, Arnold L.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [36] Copper-Catalyzed Alkylation of Nitroalkanes with α-Bromonitriles: Synthesis of β-Cyanonitroalkanes
    Shimkin, Kirk W.
    Gildner, Peter G.
    Watson, Donald A.
    [J]. ORGANIC LETTERS, 2016, 18 (05) : 988 - 991
  • [37] Copper-catalyzed asymmetric propargylic substitution with salicylaldehyde-derived imine esters
    Wang, Ruo-Qing
    Shen, Chong
    Cheng, Xiang
    Dong, Xiu-Qin
    Wang, Chun-Jiang
    [J]. CHEMICAL COMMUNICATIONS, 2022, 58 (61) : 8552 - 8555
  • [38] Synthesis and Structure of Intermediates in Copper-Catalyzed Alkylation of Diphenylphosphine
    Cain, Matthew F.
    Hughes, Russell P.
    Glueck, David S.
    Golen, James A.
    Moore, Curtis E.
    Rheingold, Arnold L.
    [J]. INORGANIC CHEMISTRY, 2010, 49 (17) : 7650 - 7662
  • [39] Synthesis of Quaternary Carbon Stereocenters by Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Arylboronates
    Takeda, Momotaro
    Takatsu, Keishi
    Shintani, Ryo
    Hayashi, Tamio
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (06): : 2354 - 2367
  • [40] Copper-Catalyzed Enantioselective Propargylic Etherification of Propargylic Esters with Alcohols
    Nakajima, Kazunari
    Shibata, Masashi
    Nishibayashi, Yoshiaki
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) : 2472 - 2475
12345