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
  • [41] Palladium-Catalyzed Intermolecular Polarity-Mismatched Addition of Unactivated Alkyl Radicals to Unactivated Alkenes
    Wu, Xiaojin
    Xiao, Guanlin
    Ding, Yalan
    Zhan, Ying
    Zhao, Yao
    Chen, Rizhi
    Loh, Teck-Peng
    ACS CATALYSIS, 2020, 10 (23) : 14107 - 14116
  • [42] Chelation-controlled 1,3-asymmetric induction in radical addition to γ-hydroxy- and γ-alkoxy-α-methylenecarboxylic esters
    Nagano, H
    Toi, S
    Yajima, T
    SYNLETT, 1999, (01) : 53 - 54
  • [43] Open Dimer Participation in Chelation Controlled Addition of Methyllithium Dimer to a- and QQ -Alkoxy Aldehydes
    Chem Lett, 10 (1079):
  • [44] Chelation-controlled ester-derived titanium enolate aldol reaction:: diastereoselective syn-aldols with mono- and bidentate aldehydes
    Ghosh, AK
    Kim, JH
    TETRAHEDRON LETTERS, 2002, 43 (32) : 5621 - 5624
  • [45] Reactivity of arynes toward functionalized alkenes: intermolecular Alder-ene vs. addition reactions
    Gupta, Saswata
    Xie, Peipei
    Xia, Yuanzhi
    Lee, Daesung
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (14): : 2208 - 2213
  • [46] Highly stereoselective addition to alkoxy or hydroxy ketones using an α-stannyl ester-stannous chloride system in a chelation-controlled manner
    Yasuda, M
    Okamoto, K
    Sako, T
    Baba, A
    CHEMICAL COMMUNICATIONS, 2001, (02) : 157 - 158
  • [47] Practical synthesis of C1-8 fragment of autolytimycin via a chelation-controlled diastereoselective addition of diisopropenylzinc to α-methoxy aldehyde
    Yang, Fan
    Feng, Liang
    Wang, Nengzhong
    Liu, Xuge
    Li, Jun
    Shen, Yuehai
    TETRAHEDRON, 2013, 69 (45) : 9463 - 9468
  • [48] ASYMMETRIC HETERO-DIELS-ALDER REACTION OF ALPHA-ALKOXY ALDEHYDES WITH ACTIVATED DIENES - THE SCOPE OF LEWIS ACID CHELATION-CONTROLLED CYCLOADDITIONS
    MIDLAND, MM
    KOOPS, RW
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17): : 5058 - 5065
  • [49] A second-generation catalyst for intermolecular hydroacylation of alkenes and Alkynes using β-S-substituted aldehydes:: The role of a hemilabile P-O-P ligand
    Moxham, Gemma L.
    Randell-Sly, Helen E.
    Brayshaw, Simon K.
    Woodward, Robert L.
    Weller, Andrew S.
    Willis, Michael C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) : 7618 - 7622
  • [50] Synthesis of highly functionalized propargylic alcohols:: Direct addition of epoxy acetylides to aldehydes and ketones
    Hoffmann-Röder, A
    Krause, N
    HELVETICA CHIMICA ACTA, 2002, 85 (10) : 3176 - 3184
12345