Samarium-Mediated Asymmetric Synthesis

被引:3
|
作者
Majee, Suman [1 ]
Ray, Devalina [1 ,2 ]
Banik, Bimal Krishna [3 ]
机构
[1] Amity Univ, Amity Inst Click Chem Res & Studies, Sect 125, Noida 201313, India
[2] Amity Univ, Amity Inst Biotechnol, Sect 125, Noida 201313, India
[3] Prince Mohammad Bin Fahd Univ, Coll Sci & Human Studies, Dept Math & Nat Sci, Dhahran 34754, Saudi Arabia
关键词
samarium; asymmetric reactions; radical cyclization; cascade reactions; RADICAL CYCLIZATION CASCADES; ORGANIC-SYNTHESIS; REDUCING POWER; STEREOSELECTIVE CYCLIZATION; DIIODIDE; REDUCTION; IODIDE; SMI2; CHEMISTRY; KETONES;
D O I
10.3390/catal13010024
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Samarium is an efficient reducing agent, a radical generator in cyclization and a cascade addition reaction. Interestingly, samarium metal has crucial impact on numerous C-C and C-X (X = hetero atom) bond forming transformations. It has been established as an exceptional chemo-selective and stereoselective reagent. The reactivity of the samarium catalyst/reagent is remarkably enhanced in the presence of various additives, ligands and solvents through effective coordination and an increase in reduction potential. It has inherent character to act as electron donor for a wide range of transformations including the asymmetric version of various reactions. This review accentuates the developments in samarium-mediated/catalyzed asymmetric organic synthesis over the past 12 years, where the chirality has been induced from ligand, a nearby asymmetric center within the substrate or through coordination directed stereospecific reactions.
引用
收藏
页数:26
相关论文
共 50 条
  • [1] SYNTHESIS OF ALKYNYLSILANES BY SAMARIUM-MEDIATED ALKYLATION OF ETHYNYLSILANES
    MURAKAMI, M
    HAYASHI, M
    ITO, Y
    SYNLETT, 1994, (03) : 179 - 180
  • [2] Samarium-mediated mild and facile method for the synthesis of amides
    Shi, Feng
    Li, Jian
    Li, Chunju
    Jia, Xueshun
    TETRAHEDRON LETTERS, 2010, 51 (46) : 6049 - 6051
  • [3] Samarium Diiodide/Samarium-Mediated Deoxygenative Hydrosilylation of Ketones
    Li, Ruxing
    Ma, Yilin
    Zhang, Jianwen
    Liu, Chengwei
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (23): : 17418 - 17424
  • [4] Samarium Diiodide/Samarium-mediated Deoxygenative Hydroborylation of Aldehydes
    Liu, Chengwei
    Ma, Yilin
    Zhou, Wei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (13)
  • [5] Chemoselective Samarium-Mediated Benzoyloxysulfone Eliminations
    Volz, Erasmus O.
    O'Neil, Gregory W.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (20): : 8428 - 8432
  • [6] Total synthesis of honokiol by selective samarium-mediated allylic benzoate reduction
    Wright, Alicia M.
    O'Neil, Gregory W.
    TETRAHEDRON LETTERS, 2016, 57 (31) : 3441 - 3443
  • [7] Samarium-mediated elimination/isomerization of allylic benzoates
    Roberts, Connor L.
    Volz, Erasmus O.
    O'Neil, Gregory W.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [8] Samarium-mediated Barbier reaction of carbonyl compounds
    Basu, MK
    Banik, BK
    TETRAHEDRON LETTERS, 2001, 42 (02) : 187 - 189
  • [9] SAMARIUM-MEDIATED ACYCLIC STEREOSELECTION IN A RADICAL REACTION
    INANAGA, J
    UJIKAWA, O
    HANDA, Y
    OTSUBO, K
    YAMAGUCHI, M
    JOURNAL OF ALLOYS AND COMPOUNDS, 1993, 192 (1-2) : 197 - 199
  • [10] Samarium-mediated β-elimination in dihalo alcohols:: Diastereoselective synthesis of (Z)-vinyl halides
    Concellón, JM
    Bernad, PL
    Pérez-Andrés, JA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (16) : 2384 - 2386