Enantio- and Regioselective Conjugate Addition of Organometallic Reagents to Linear Polyconjugated Nitroolefins

被引:28
|
作者
Tissot, Matthieu [1 ]
Alexakis, Alexandre [1 ]
机构
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
基金
瑞士国家科学基金会; 新加坡国家研究基金会;
关键词
asymmetric catalysis; conjugate addition; copper; ligand effects; phosphine ligands; ACCEPTOR-SUBSTITUTED ENYNES; DIALKYLZINC REAGENTS; 1,6-CONJUGATE ADDITION; MECHANISM; ALLENES; 1,4-ADDITION; NITROALKENES; DIETHYLZINC; ROUTE;
D O I
10.1002/chem.201300538
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The copper-catalysed conjugate addition of trialkylaluminium and dialkylzinc reagents to polyconjugated nitroolefins (nitrodiene and nitroenyne derivatives) is reported. A reversed Josiphos ligand L7 allows for the selective 1,4- or 1,6-addition with high enantioselectivities.
引用
收藏
页码:11352 / 11363
页数:12
相关论文
共 50 条
  • [21] Regioselective 1,4-conjugate addition reactions of organozincate reagents to nitrodienes
    Dhakal, Ramesh C.
    Dieter, R. Karl
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [22] Novel tartrate-derived guanidine-catalyzed highly enantio- and diastereoselective Michael addition of 3-substituted oxindoles to nitroolefins
    Zou, Liwei
    Bao, Xiaoze
    Ma, Yuanyuan
    Song, Yuming
    Qu, Jingping
    Wang, Baomin
    CHEMICAL COMMUNICATIONS, 2014, 50 (43) : 5760 - 5762
  • [23] Organocatalytic Desymmetric Conjugate Addition to Cyclobutanone: An Enantio- and Diastereoselective Synthesis of [6,5,4]-Fused Carbocycles
    Panda, Shibaram
    Gayen, Upasana
    Ghorai, Prasanta
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (24)
  • [24] Stereoselective Conjugate Addition-Enamination of α-Linear N - Tert -Butanesulfinyl Ketimines with Nitroolefins
    Yisimayili, Nuermaimaiti
    Chu, Li-Feng
    Feng, Jie
    Lu, Chong-Dao
    Synthesis (Germany), 2022, 54 (19) : 4361 - 4370
  • [25] Highly enantio- and diastereoselective Michael addition of cyclohexanone to nitroolefins catalyzed by a chiral glucose-based bifunctional secondary amine-thiourea catalyst
    Lu, Aidang
    Gao, Peng
    Wu, Yang
    Wang, Youming
    Zhou, Zhenghong
    Tang, Chuchi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (15) : 3141 - 3147
  • [26] ASYMMETRIC CONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL ALPHA,BETA-UNSATURATED ESTERS
    FANG, CL
    OGAWA, T
    SUEMUNE, H
    SAKAI, K
    TETRAHEDRON-ASYMMETRY, 1991, 2 (05) : 389 - 398
  • [27] Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents
    Goncalves-Contal, Sylvie
    Gremaud, Ludovic
    Palais, Laetitia
    Babel, Lucille
    Alexakis, Alexandre
    SYNTHESIS-STUTTGART, 2016, 48 (19): : 3301 - 3308
  • [28] Regioselective 1,6-Conjugate Addition of Boronic Acids and Grignard Reagents to Dienylpyridines
    Roscales, Silvia
    Salado, Irene G.
    Csaky, Aurelio G.
    SYNLETT, 2011, (15) : 2234 - 2236
  • [29] Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors
    Pichon, Delphine
    Morvan, Jennifer
    Crevisy, Christophe
    Mauduit, Marc
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 212 - 232
  • [30] Unprecedented copper-catalyzed asymmetric conjugate addition of organometallic reagents to α,β-unsaturated lactams
    Pineschi, M
    Del Moro, F
    Gini, F
    Minnaard, AJ
    Feringa, BL
    CHEMICAL COMMUNICATIONS, 2004, (10) : 1244 - 1245