The [1,2]- and [1,4]-Wittig rearrangement

被引：13
|
作者：
Wang, Fan [1 ]
Wang, Juhui [1 ]
Zhang, Yan [1 ]
Yang, Jingyue [1 ]
机构：
[1] Yanshan Univ, Sch Environm & Chem Engn, Hebei Key Lab Appl Chem, Qinhuangdao 066004, Hebei, Peoples R China
来源：
TETRAHEDRON | 2020年 / 76卷 / 05期
关键词：
1,4-Wittig rearrangement; 1,4]-Wittig rearrangement; Mechanism; Scope; Stereochemistry; Application; DEFINED ALPHA-ALKOXYALKYLLITHIUMS; IMINO 1,2-WITTIG REARRANGEMENT; BENZYL ETHERS INHIBITION; WITTIG REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; FORMAL SYNTHESIS; ABSOLUTE-CONFIGURATION; TANDEM; MECHANISM; SYSTEM;
D O I：
10.1016/j.tet.2019.130857
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This review traces the development of the [1,2]- and [1,4]-Wittig rearrangement and their applications in organic synthesis for the past twenty years. The mechanisms are discussed along with detailed analysis of reaction scope and stereochemistry. Applications are reviewed in the context of synthesis of chiral ligands, ring constriction reactions and tandem reactions with the [1,2]-/[1,4]-Wittig rearrangements involved, etc. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页数：12
相关论文
共 50 条
  • [1] Mechanistic investigation in the [1,4] and [1,2] Wittig rearrangement reactions: a DFT study
    Nath, Shilpa R. .
    Joshi, Kaustubh A.
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2018, 20 (33) : 21457 - 21473
  • [2] [1,2]-WITTIG REARRANGEMENT OF AROMATIC HETEROCYCLES
    Yang, Jingyue
    Wangweerawong, Apiwat
    Dudley, Gregory B.
    HETEROCYCLES, 2012, 85 (07) : 1603 - +
  • [3] Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans
    Mori-Quiroz, Luis M.
    Maloba, Emmanuel W.
    Maleczka, Robert E., Jr.
    ORGANIC LETTERS, 2021, 23 (15) : 5724 - 5728
  • [4] Access to new steroids via a (1,2) Wittig rearrangement
    Stéphan, E
    Dousset, M
    Foy, N
    Jaouen, G
    JOURNAL OF CHEMICAL RESEARCH-S, 2002, (10): : 506 - 507
  • [5] Further Studies on the [1,2]-Wittig Rearrangement of 2-(2-Benzyloxy)aryloxazolines
    Aitken, R. Alan
    Harper, Andrew D.
    Inwood, Ryan A.
    MOLECULES, 2022, 27 (10):
  • [6] Cobalt-catalysed [1,2]-Wittig rearrangement of ethers to secondary alcohols
    Pattanaik, Sandip
    Kumar, Anurag
    Gunanathan, Chidambaram
    CHEMICAL COMMUNICATIONS, 2023, 59 (13) : 1853 - 1856
  • [7] [1,2]- vs [2,3]-Wittig Rearrangement in Carbohydrate Derived Alkenyl Systems
    Perali, Ramu Sridhar
    Boddu, Umamaheswara Rao
    Sankar, Drisya Chittadi
    ORGANIC LETTERS, 2021, 23 (10) : 3850 - 3853
  • [8] Exploring the Reactivity of α-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited
    Velasco, Rocio
    Silva Lopez, Carlos
    Nieto Faza, Olalla
    Sanz, Roberto
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (42) : 15058 - 15068
  • [9] Stereoselective One-pot 1,4-Elimination and the [1,2]-Wittig Rearrangement of (E)-δ-(Arylmethoxy or 3-Silyl-2-propynyloxy)-substituted Allylic Sulfones
    Horii, Susumu
    Ishimaru, Isao
    Ukaji, Yutaka
    Inomata, Katsuhiko
    CHEMISTRY LETTERS, 2011, 40 (05) : 521 - 523
  • [10] [1,2]-Wittig Rearrangement of THP Acetal Compounds: Facile Synthesis of Aromatic Tertiary Alcohols
    Gu, Feng-Lei
    Liu, Lu-Xin
    Lai, Guo-Qiao
    Jiang, Jian-Xiong
    Sheng, Chun-Qi
    Qiu, Hua-Yu
    Xu, Li-Wen
    ORGANIC COMMUNICATIONS, 2011, 4 (01) : 9 - 17
12345