Copper-Catalyzed Regio- and Enantioselective Synthesis of Chiral Enol Acetates and β-Substituted Aldehydes

被引：34
|
作者：
Fananas-Mastral, Martin [1 ]
Feringa, Ben L. [1 ]
机构：
[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 38期
关键词：
ASYMMETRIC CONJUGATE ADDITION; LIGANDS; KETONES;
D O I：
10.1021/ja105585y
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The in situ transformation of alpha,beta-unsaturated aldehydes into alpha-chloroallylic acetates and subsequent copper-catalyzed regio- and enantioselective (up to 94% ee) allylic alkylation with Grignard reagents provides chiral enol acetates and chiral beta-substituted aldehydes in a one-pot protocol.
引用
收藏
页码：13152 / 13153
页数：2
相关论文
共 50 条
  • [31] Copper-Catalyzed Coupling of Oxime Acetates with Aldehydes: A New Strategy for Synthesis of Pyridines
    Ren, Zhi-Hui
    Zhang, Zhi-Yuan
    Yang, Bing-Qin
    Wang, Yao-Yu
    Guan, Zheng-Hui
    ORGANIC LETTERS, 2011, 13 (19) : 5394 - 5397
  • [32] Highly Regio- and Stereoselective Synthesis of Boron-Substituted Enynes via Copper-Catalyzed Borylation of Conjugated Diynes
    Li, DingXi
    Kim, Yeong Eun
    Yun, Jaesook
    ORGANIC LETTERS, 2015, 17 (04) : 860 - 863
  • [33] Copper-Catalyzed Regio- and Stereoselective Hydrothiolation of Allenamides, Enamides, and Ynamides
    Pages, Lucas
    Bouquin, Maxime
    Jaroschik, Florian
    Monnier, Florian
    Taillefer, Marc
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (02): : 1168 - 1176
  • [34] Regio- and stereoselective copper-catalyzed β-borylation of allenoates by a preactivated diboron
    Thorpe, Steven B.
    Guo, Xi
    Santos, Webster L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [35] Regio- and stereoselective copper-catalyzed β-borylation of allenoates by a preactivated diboron
    Thorpe, Steven B.
    Guo, Xi
    Santos, Webster L.
    CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 424 - 426
  • [36] Copper-Catalyzed Regio- and Stereoselective O-Arylation of Enolates
    Xu, Ze-Feng
    Cai, Chen-Xin
    Jiang, Min
    Liu, Jin-Tao
    ORGANIC LETTERS, 2014, 16 (13) : 3436 - 3439
  • [37] Copper-catalyzed enantioselective propargylic substitution of propargylic acetates with enamines
    Wang, Bo
    Liu, Chunxiao
    Guo, Hongchao
    RSC ADVANCES, 2014, 4 (95): : 53216 - 53219
  • [38] Regio- and stereoselective copper-catalyzed synthesis of vicinal haloamino ketones from α,β-unsaturated ketones
    Chen, DJ
    Timmons, C
    Chao, S
    Li, GG
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (14) : 3097 - 3101
  • [39] Copper-Catalyzed Synthesis of Tetrasubstituted Enynylboronates via Chemo-, Regio-, and Stereoselective Borylalkynylation
    Han, Jung Tae
    Yun, Jaesook
    ORGANIC LETTERS, 2018, 20 (07) : 2104 - 2107
  • [40] Regio- and enantioselective direct oxyamination reaction of aldehydes catalyzed by α,α-diphenylprolinol trimethylsilyl ether
    Palomo, Claudio
    Vera, Silvia
    Velilla, Irene
    Mielgo, Antonia
    Gomez-Bengoa, Enrique
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (42) : 8054 - 8056
12345