Palladium-catalyzed allylic alkylation enabled by ketone umpolung via Pudovik addition/[1,2]-phospha-Brook rearrangement

被引：0
|
作者：
Jian Zhang [1 ]
Jia-Yi Su [2 ]
Yang-Zi Liu [1 ]
Hao Li [2 ]
Quannan Wang [1 ]
Wei-Ping Deng [1 ,2 ]
机构：
[1] College of Chemistry and Materials Science, Zhejiang Normal University
[2] School of Pharmacy, East China University of Science and Technology
来源：
Science China(Chemistry) | 2023年 / 10期
关键词：
D O I：
暂无
中图分类号：
O621.251 [];
学科分类号：
摘要：
Palladium-catalyzed allylic alkylation enabled by ketone umpolung via Pudovik addition/[1,2]-phospha-Brook rearrangement with phosphites has been developed. The protocol offers a straightforward method for the synthesis of potentially bioactive homoallylic alcohol phosphonates in an efficient and economical way. This cascade reaction proceeds under mild conditions with excellent functional group compatibility. Furthermore, the catalytic asymmetric version has also been explored.
引用
收藏
页码：2810 / 2816
页数：7
相关论文
共 50 条
  • [1] Palladium-catalyzed allylic alkylation enabled by ketone umpolung via Pudovik addition/[1,2]-phospha-Brook rearrangement
    Jian Zhang
    Jia-Yi Su
    Yang-Zi Liu
    Hao Li
    Quannan Wang
    Wei-Ping Deng
    Science China Chemistry, 2023, 66 : 2810 - 2816
  • [2] Palladium-catalyzed allylic alkylation enabled by ketone umpolung via Pudovik addition/[1,2]-phospha-Brook rearrangement
    Jian Zhang
    JiaYi Su
    YangZi Liu
    Hao Li
    Quannan Wang
    WeiPing Deng
    Science China(Chemistry), 2023, 66 (10) : 2810 - 2816
  • [3] Palladium-catalyzed allylic alkylation enabled by ketone umpolung via Pudovik addition/[1,2]-phospha-Brook rearrangement
    Zhang, Jian
    Su, Jia-Yi
    Liu, Yang-Zi
    Li, Hao
    Wang, Quannan
    Deng, Wei-Ping
    SCIENCE CHINA-CHEMISTRY, 2023, 66 (10) : 2810 - 2816
  • [4] Stereoselective Reductive Coupling Reactions Utilizing [1,2]-Phospha-Brook Rearrangement: A Powerful Umpolung Approach
    Kaur, Ravneet
    Singh, Ravi P.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15): : 10325 - 10338
  • [5] Bronsted base-catalyzed 1,2-addition/[1,2]-phospha-Brook rearrangement sequence providing functionalized phosphonates
    Kondoh, Azusa
    Terada, Masahiro
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (14) : 2863 - 2866
  • [6] Umpolung Phosphorylation of Tyrosine via 1,2-Phospha-Brook Rearrangement
    Fukuta, Tomoyuki
    Tatsumi, Toshifumi
    Fujiyoshi, Kohei
    Koyama, Takashi
    Kawashima, Shigehiro A.
    Mitsunuma, Harunobu
    Yamatsugu, Kenzo
    Kanai, Motomu
    ORGANIC LETTERS, 2024, 26 (41) : 8827 - 8831
  • [7] Organocatalytic Arylation of α-Ketoesters Based on Umpolung Strategy: Phosphazene-Catalyzed SNAr Reaction Utilizing [1,2]-Phospha-Brook Rearrangement
    Kondoh, Azusa
    Aoki, Takuma
    Terada, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (50) : 13110 - 13113
  • [8] Bronsted base-catalyzed α-oxygenation of carbonyl compounds utilizing the [1,2]-phospha-Brook rearrangement
    Kondoh, Azusa
    Terada, Masahiro
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (07): : 801 - 805
  • [9] A diastereoselective strategy for dihydrophenanthrene-fused spirooxindoles via [1,2]-phospha-Brook rearrangement
    Ali, Amjad
    Harit, Harish K.
    Behera, Chandana
    Singh, Ravi P.
    CHEMICAL COMMUNICATIONS, 2024, 60 (67) : 8904 - 8907
  • [10] Intramolecular Cyclization of Alkynyl α-Ketoanilide Utilizing [1,2]-Phospha-Brook Rearrangement Catalyzed by Phosphazene Base
    Kondoh, Azusa
    Aoki, Takuma
    Terada, Masahiro
    ORGANIC LETTERS, 2014, 16 (13) : 3528 - 3531
12345