Organocatalytic enantioselective Mukaiyama-Mannich reaction of fluorinated enol silyl ethers and cyclic N-sulfonyl ketimines

被引：75
|
作者：
Yu, Jin-Sheng [1 ]
Zhou, Jian [1 ,2 ]
机构：
[1] E China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, 3663N Zhongshan Rd, Shanghai 200062, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2016年 / 3卷 / 03期
关键词：
CATALYZED NUCLEOPHILIC ALLYLATION; ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; HIGHLY EFFICIENT; DIFLUOROENOL SILYL; STEREOSELECTIVE-SYNTHESIS; TRIFLUOROMETHYL KETONES; ALDOL REACTION; CONSTRUCTION;
D O I：
10.1039/c5qo00407a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first catalytic asymmetric Mukaiyama-Mannich reaction of fluorinated silyl enol ethers and ketimines is developed. Under the catalysis of hydroquinine derived bifunctional urea, cyclic N-sulfonyl ketimines readily react with fluorinated enol silyl ethers to afford benzosultam based C-alpha-tetrasubstituted alpha-amino acid derivatives featuring a fluoroalkyl group in high to excellent yields and stereoselectivities.
引用
收藏
页码：298 / 303
页数：6
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  • [1] Ni(II)-Catalyzed enantioselective Mukaiyama-Mannich reaction between silyl enol ethers and cyclic N-sulfonyl α-ketiminoesters
    Xie, Lei
    Ma, Hongli
    Li, Jiaqi
    Yu, Yuan
    Qin, Zhaohai
    Fu, Bin
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (09): : 1858 - 1862
  • [2] Enantioselective Imino-Ene Reaction of N-Sulfonyl Ketimines with Silyl Enol Ethers: Access to Chiral Benzosultams
    Hou, Liuzhen
    Kang, Tengfei
    Yang, Liangkun
    Cao, Weidi
    Feng, Xiaoming
    [J]. ORGANIC LETTERS, 2020, 22 (04) : 1390 - 1395
  • [3] Enantioselective Mannich Reaction between Cyclic N-Sulfonyl Ketimines and Isatin-Derived Ketimines
    Mei, Yao-Yao
    Xu, Chong-Xiao
    Sha, Feng
    Hao, Shilong
    Liu, Shunying
    Wu, Xin-Yan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13272 - 13283
  • [4] Calcium catalyzed Mukaiyama-Mannich addition of silyl enol ethers to nitrones
    Congdon, Elizabeth A.
    Nolin, Kristine A.
    [J]. CATALYSIS COMMUNICATIONS, 2016, 79 : 35 - 38
  • [5] A Highly Efficient Gold(I)-Catalyzed Mukaiyama-Mannich Reaction of α-Amino Sulfones with Fluorinated Silyl Enol Ethers To Give β-Amino α-Fluorinated Ketones
    Hu, Xiao-Si
    Du, Yi
    Yu, Jin-Sheng
    Liao, Fu-Min
    Ding, Pei-Gang
    Zhou, Jian
    [J]. SYNLETT, 2017, 28 (16) : 2194 - 2198
  • [6] A highly efficient Mukaiyama-Mannich reaction of N-Boc isatin ketimines and other active cyclic ketimines using difluoroenol silyl ethers catalyzed by Ph3PAuOTf
    Yu, Jin-Sheng
    Zhou, Jian
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (45) : 10968 - 10972
  • [7] Enantioselective organocatalytic Mukaiyama-Michael addition of silyl enol ethers to α,β-unsaturated aldehydes
    Wang, W
    Li, H
    Wang, J
    [J]. ORGANIC LETTERS, 2005, 7 (08) : 1637 - 1639
  • [8] Organocatalytic Enantioselective Synthesis of Polycyclic Benzosultams from 2-Amino-β-nitrostyrenes with Cyclic N-Sulfonyl Ketimines
    Kim, Yoseop
    Han, Ji Won
    Kim, Sung-Gon
    [J]. ORGANIC LETTERS, 2024, 26 (07) : 1472 - 1477
  • [9] Organocatalytic Enantioselective Mukaiyama-Mannich Reaction of Isatin-Derived Ketimines for the Synthesis of Oxindolyl-β3, 3-Amino Acid Esters
    Hajra, Saumen
    Laskar, Sujay
    Janata, Bibekananda
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (64) : 14688 - 14693
  • [10] Internally reuse by-product as promoter: A catalyst-free imine formation/Mukaiyama-Mannich sequence of α-amido sulfones with fluorinated silyl enol ethers
    Hu, Xiao-Si
    Yu, Jin-Sheng
    Gong, Yi
    Zhou, Jian
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2019, 219 : 106 - 114
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