Chemoselective, Regioselective, and Enantioselective Allylations of NH2OH under Iridium Catalysis

被引：5
|
作者：
Chen, Jiteng [1 ]
Liang, Qingchun [1 ]
Zhao, Xiaoming [1 ]
机构：
[1] Tongji Univ, Sch Chem Technol & Engn, 1239 Siping Rd, Shanghai 200092, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 14期
基金：
美国国家科学基金会;
关键词：
ALLYLIC AMINATION; CONJUGATE ADDITION; CHIRAL LIGANDS; AMMONIA; SUBSTITUTION; HYDROXYLAMINE; REARRANGEMENT; DERIVATIVES; COMPLEXES; REAGENTS;
D O I：
10.1021/acs.orglett.9b01357
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The utilization of unprotected NH2OH, which is not only an oxygen nucleophile but also a nitrogen nucleophile, in iridium catalyzed allylic substitution is realized under mild conditions. The chemoselectivity, stereoselectivity, and multiple allylation are controlled by adjusting the reaction conditions. This method produces the N-(1-allyl)-hydroxylamines in good to high yields with high level of chemoselectivities, regioselectivities, and enantioselectivities. The application of allylated hydroxylamine (R)-3a in the synthesis of diallylated hydroxylamine 6 is achieved, along with an excellent diastereomeric ratio.
引用
收藏
页码：5383 / 5386
页数：4
相关论文
共 50 条
  • [31] GIANT REORGANIZATION ENERGY IN THE OXIDATION OF NH2OH WITH IRCL6(2-)
    HUNG, ML
    MCKEE, ML
    STANBURY, DM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 160 - INOR
  • [32] BROAD VIBRATIONAL OVERTONE LINEWIDTHS IN THE 7-NU-OH BAND OF ROTATIONALLY SELECTED NH2OH
    LUO, X
    FLEMING, PR
    SECKEL, TA
    RIZZO, TR
    JOURNAL OF CHEMICAL PHYSICS, 1990, 93 (12): : 9194 - 9196
  • [33] EQUILIBRIUM GEOMETRIES, INTERNAL-ROTATION POTENTIALS, AND SPECTROSCOPIC CONSTANTS IN NH2OH, NH2OF, NHFOH, AND NHFOF
    TYRRELL, J
    LEWISBEVAN, W
    KRISTIANSEN, D
    JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (49): : 12768 - 12772
  • [34] Formation of Hydroxylamine (NH2OH) in Electron-Irradiated Ammonia-Water Ices
    Zheng, Weijun
    Kaiser, Ralf I.
    JOURNAL OF PHYSICAL CHEMISTRY A, 2010, 114 (16): : 5251 - 5255
  • [35] Theoretical study on the mechanism and kinetics of atmospheric reactions NH2OH + OOH and NH2CH3 + OOH
    Valadbeigi, Younes
    Farrokhpour, Hossein
    Tabrizchi, Mahmoud
    PHYSICS LETTERS A, 2014, 378 (10) : 777 - 784
  • [36] Terahertz rotational spectra of NH2OH in the ground and some low excited vibrational states
    Morino, I
    Yamada, KMT
    Klein, H
    Belov, SP
    Winnewisser, G
    Bocquet, R
    Wlodarczak, G
    Lodyga, W
    Kreglewski, M
    JOURNAL OF MOLECULAR STRUCTURE, 2000, 517 : 367 - 373
  • [37] Electrosynthesis of aminotelechelic poly(acrylamide): Initiated by Ti(III)-NH2OH redox system
    Padmalatha, M
    Sherigara, BS
    INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 1997, 36 (08): : 722 - 724
  • [38] Theoretical Insights into the Selectivity of Nitrite Reduction to NH2OH on Single-Atom Catalysts
    Zheng, Wei
    Fan, Dingge
    Yang, Yang
    Chen, Qianwang
    NANO LETTERS, 2024, 24 (29) : 9011 - 9016
  • [39] Enantioselective Direct Vinylogous Allylic Alkylation of 4-Methylquinolones under Iridium Catalysis
    Sarkar, Rahul
    Mukherjee, Santanu
    ORGANIC LETTERS, 2019, 21 (13) : 5315 - 5320
  • [40] THEORETICAL INVESTIGATIONS OF THE NATURE OF INTRAMOLECULAR INTERACTIONS .2. APPLICATION OF THE ENERGY DECOMPOSITION SCHEME TO CH3NH2, CH3OH, NH2NH2, NH2OH AND HOOH
    SMITS, GF
    KROL, MC
    ALTONA, C
    MOLECULAR PHYSICS, 1988, 63 (05) : 921 - 938
12345