Palladium/sulfoxide-phosphine-catalyzed highly enantioselective allylic etherification and amination

被引：47
|
作者：
Feng, Bin [1 ,2 ]
Cheng, Hong-Gang [1 ,2 ]
Chen, Jia-Rong [1 ,2 ]
Deng, Qiao-Hui [1 ,2 ]
Lu, Liang-Qiu [1 ,2 ]
Xiao, Wen-Jing [1 ,2 ]
机构：
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 67期
基金：
美国国家科学基金会;
关键词：
RING-CLOSING METATHESIS; ASYMMETRIC-SYNTHESIS; HYBRID LIGANDS; ALKYLATION; ALCOHOLS; SUBSTITUTION; DERIVATIVES; ALLYLATION; COMPLEX; VERSATILE;
D O I：
10.1039/c4cc03920c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The Pd/sulfoxide-phosphine-catalyzed highly enantioselective allylic etherification and amination with a wide range of O- and N-nucleophiles have been developed (up to 97% yield, 985% ee). The products can also be conveniently transformed into biologically active chiral heterocycles.
引用
收藏
页码：9550 / 9553
页数：4
相关论文
共 50 条
  • [21] New chiral phosphine-phosphite ligands in the enantioselective palladium-catalyzed allylic alkylation
    Deerenberg, S
    Schrekker, HS
    van Strijdonck, GPF
    Kamer, PCJ
    van Leeuwen, PWNM
    Fraanje, J
    Goubitz, K
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16): : 4810 - 4817
  • [22] Palladium catalyzed enantioselective rearrangement of allylic imidates to allylic amides
    Hollis, TK
    Overman, LE
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 290 - 299
  • [23] PALLADIUM-CATALYZED, ENANTIOSELECTIVE ALLYLIC SUBSTITUTIONS
    REISER, O
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04): : 547 - 549
  • [24] Palladium-Catalyzed Enantioselective Allylic Substitution
    Milhau, Ludovic
    Guiry, Patrick J.
    TRANSITION METAL CATALYZED ENANTIOSELECTIVE ALLYLIC SUBSTITUTION IN ORGANIC SYNTHESIS, 2012, 38 : 95 - 153
  • [25] Palladium-catalyzed enantioselective allylic phosphination
    Butti, Pietro
    Rochat, Raphael
    Sadow, Aaron D.
    Togni, Antonio
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) : 4878 - 4881
  • [26] Palladium/BINAP(S)-catalyzed asymmetric allylic amination
    Faller, JW
    Wilt, JC
    ORGANIC LETTERS, 2005, 7 (04) : 633 - 636
  • [27] PALLADIUM(0)-CATALYZED ALLYLIC ALKYLATION AND AMINATION OF ALLYLNITROALKANES
    TAMURA, R
    HEGEDUS, LS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) : 3727 - 3729
  • [28] Direct, Enantioselective Iridium-Catalyzed Allylic Amination of Racemic Allylic Alcohols
    Lafrance, Marc
    Roggen, Markus
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (14) : 3470 - 3473
  • [29] Chiral phosphine-catalyzed regio- and enantioselective allylic amination of Morita-Baylis-Hillman acetates
    Ma, Guang-Ning
    Cao, Shu-Hua
    Shi, Min
    TETRAHEDRON-ASYMMETRY, 2009, 20 (09) : 1086 - 1092
  • [30] Direct use of allylic alcohols and allylic amines in palladium-catalyzed allylic amination
    Jing, Jiangyan
    Huo, Xiaohong
    Shen, Jiefeng
    Fu, Jingke
    Meng, Qinghua
    Zhang, Wanbin
    CHEMICAL COMMUNICATIONS, 2017, 53 (37) : 5151 - 5154
12345