Chelation-controlled intermolecular hydroacylation: Direct addition of alkyl aldehydes to functionalized alkenes

被引：123
|
作者：
Willis, MC [1 ]
McNally, SJ
Beswick, PJ
机构：
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
[2] GlaxoSmithKline, Med Res Ctr, Neurol Ctr Excellence Drug Discovery, Stevenage SG1 2NY, Herts, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 03期
关键词：
aldehydes; alkenes; homogeneous catalysis; hydroacylation; rhodium;
D O I：
10.1002/anie.200352751
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The pendant methylsulfanyl group of aldehyde 1 provides chelation stabilization (see 3), thus allowing direct hydroacylation of functionalized electron-poor alkenes 2 in good yields under mild conditions. Electron-deficient alkynes can also be used as substrates. R = ester, arnide, imide, sulfone; dppe = 1,2-bis(diphenylphosphanyl)ethane.
引用
收藏
页码：340 / 343
页数：4
相关论文
共 50 条
  • [1] Chelation-controlled intermolecular alkene and alkyne hydroacylation:: The utility of β-thioacetal aldehydes
    Willis, MC
    Randell-Sly, HE
    Woodward, RL
    Currie, GS
    ORGANIC LETTERS, 2005, 7 (11) : 2249 - 2251
  • [2] Traceless Chelation-Controlled Rhodium-Catalyzed Intermolecular Alkene and Alkyne Hydroacylation
    Hooper, Joel F.
    Young, Rowan D.
    Weller, Andrew S.
    Willis, Michael C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (09) : 3125 - 3130
  • [3] Chelation-controlled addition of dialkylzines to trans-α,β-epoxy aldehydes
    Urabe, Hirokazu
    Evin, Ozden Ozel
    Sato, Fumie
    Journal of Organic Chemistry, 1995, 60 (09):
  • [4] Diastereoselective Chelation-Controlled Additions to β-Silyloxy Aldehydes
    Stanton, Gretchen R.
    Kauffman, Meara C.
    Walsh, Patrick J.
    ORGANIC LETTERS, 2012, 14 (13) : 3368 - 3371
  • [5] CHELATION-CONTROLLED ADDITION OF DIALKYLZINCS TO TRANS-ALPHA,BETA-EPOXY ALDEHYDES
    URABE, H
    EVIN, OO
    SATE, F
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09): : 2660 - 2661
  • [6] Chelation-Controlled Addition of Organozincs to α-Chloro Aldimines
    Stanton, Gretchen R.
    Norrby, Per-Ola
    Carroll, Patrick J.
    Walsh, Patrick J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) : 17599 - 17604
  • [7] Chelation-Controlled Additions to α-Silyloxy Aldehydes: An Autocatalytic Approach
    Raffier, Ludovic
    Stanton, Gretchen R.
    Walsh, Patrick J.
    ORGANIC LETTERS, 2013, 15 (24) : 6174 - 6177
  • [8] Recent Advances in Intermolecular Hydroacylation of Alkenes with Aldehydes through Rhodium Catalysis
    Guo, Rui
    Zhang, Guozhu
    SYNLETT, 2018, 29 (14) : 1801 - 1806
  • [9] Origins of stereoselectivity in the chelation-controlled addition of alkyl radicals to α-methylene-γ-oxycarboxylic acid esters
    Nagano, H
    Toi, S
    Matsuda, M
    Hirasawa, T
    Hirasawa, S
    Yajima, T
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (22): : 2525 - 2538
  • [10] The Chelation-controlled Mukaiyama Aldol Reaction of Chiral α- and β-Alkoxy Aldehydes
    Roiban, Gheorghe-Doru
    Ilie, Adriana
    Reetz, Manfred T.
    CHEMISTRY LETTERS, 2014, 43 (01) : 2 - 10
12345