Samarium diiodide-mediated reaction of organic halides with carbonyl compounds

被引:10
|
作者
Utimoto, K [1 ]
Matsubara, S [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
关键词
D O I
10.5059/yukigoseikyokaishi.56.908
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The following three types of samarium diiodide mediated reactions of organic halides and carbonyl compounds are discussed: 1) Samarium-mediated highly stereoselective reaction of 1,1-dihaloalkanes with aldehydes. 2) Stereoselective reaction with configurationally stable alpha-phenylthioalkylsamarium compounds. 3) Preparation and reaction of a samarium enolate equivalent of beta-ketoester.
引用
收藏
页码:908 / 918
页数:11
相关论文
共 50 条
  • [1] Samarium diiodide-mediated intermolecular coupling of organic halides with cyclic imides
    Farcas, S
    Namy, JL
    TETRAHEDRON LETTERS, 2001, 42 (05) : 879 - 881
  • [2] Samarium diiodide-mediated intramolecular cyclodimerisation of bis-α,β-unsaturated carbonyl compounds
    Powell, Jonathan R.
    Dixon, Sally
    Light, Mark E.
    Kilburn, Jeremy D.
    TETRAHEDRON LETTERS, 2009, 50 (26) : 3564 - 3567
  • [3] SAMARIUM(II) DIIODIDE-MEDIATED INTERMOLECULAR ALDOL-TYPE REACTION OF PHENACYL BROMIDES WITH CARBONYL-COMPOUNDS
    AOYAGI, Y
    YOSHIMURA, M
    TSUDA, M
    TSUCHIBUCHI, T
    KAWAMATA, S
    TATENO, H
    ASANO, K
    NAKAMURA, H
    OBOKATA, M
    OHTA, A
    KODAMA, Y
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (06): : 689 - 692
  • [4] HOMOALLYLIC ALCOHOLS FROM SAMARIUM DIIODIDE-MEDIATED COUPLING OF ALLYLIC SULFONES WITH CARBONYL-COMPOUNDS
    CLAYDEN, J
    JULIA, M
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (19) : 2261 - 2262
  • [5] NONTOXIC LIGANDS IN SAMARIUM DIIODIDE-MEDIATED CYCLIZATIONS
    CABRI, W
    CANDIANI, I
    COLOMBO, M
    FRANZOI, L
    BEDESCHI, A
    TETRAHEDRON LETTERS, 1995, 36 (06) : 949 - 952
  • [6] Samarium(II) Diiodide-Mediated Deoxygenation of Sulfoxides
    Gao, Yu
    Chai, Fang
    Szostak, Michal
    Liu, Chengwei
    JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [7] A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds
    Wu, Shao-Feng
    Zheng, Xiao
    Ruan, Yuan-Ping
    Huang, Pei-Qiang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (14) : 2967 - 2975
  • [8] Dipyrrolidinomethylaminophosphoric acid triamide (DPMPA) as an activator for the samarium diiodide-mediated reduction of alkyl and aryl halides
    McDonald, Chriss E.
    Ramsey, Jeremy R.
    Sampsell, David G.
    Anderson, Laura A.
    Krebs, Jordan E.
    Smith, Samantha N.
    TETRAHEDRON, 2013, 69 (14) : 2947 - 2953
  • [9] Spiranes synthesis based on samarium diiodide-mediated reductive cyclization
    Hsu, Day-Shin
    Hsu, Chi-Wei
    TETRAHEDRON LETTERS, 2012, 53 (17) : 2185 - 2188
  • [10] Samarium diiodide-mediated asymmetric reactions of 8-phenylmenthyl esters
    Fang, JM
    Chen, MY
    Shiue, JS
    Lu, L
    Hsu, JL
    TETRAHEDRON LETTERS, 2000, 41 (23) : 4633 - 4636