Iridium-Catalyzed Enantioselective Formal α-Allylic Alkylation of Acrylonitrile

被引：6
|
作者：
Roy, Pankaj [1 ]
Mukherjee, Santanu [1 ]
机构：
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, India
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 24期
关键词：
BAYLIS-HILLMAN REACTION; EFFICIENT METHOD;
D O I：
10.1021/acs.orglett.3c01552
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly enantioselective formal alpha-allylic alkylationofacrylonitrile is developed using 4-cyano-3-oxotetrahydrothiophene(c-THT) as a safe and easy-to-handle surrogate of acrylonitrile. Thistwo-step process consists of an Ir(I)/(P,olefin)-catalyzedbranched-selective allylic alkylation using easily accessible branched rac-allylic alcohols as the allylic electrophile followedby retro-Dieckmann/retro-Michael fragmentation and is shown to beapplicable for the enantioselective synthesis of alpha-allylic acrylatesas well as alpha-allylic acrolein.
引用
收藏
页码：4520 / 4524
页数：5
相关论文
共 50 条
  • [31] Iridium-Catalyzed Enantioselective Allylic Substitution of Vinylcyclopropanes by Carboxylic Acids
    Adhikari, Amit Singh
    Pandit, Soumen
    Kant, Ruchir
    Majumdar, Nilanjana
    ACS CATALYSIS, 2023, 13 (09) : 6261 - 6267
  • [32] Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation
    Alexakis, A
    Polet, D
    ORGANIC LETTERS, 2004, 6 (20) : 3529 - 3532
  • [33] Iridium-Catalyzed Allylic Substitution
    Hartwig, John F.
    Pouy, Mark J.
    IRIDIUM CATALYSIS, 2011, 34 : 169 - 208
  • [34] Regio- and enantioselective iridium-catalyzed allylic alkylation with in situ activated P,C-chelate complexes
    Lipowsky, G
    Miller, N
    Helmchen, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (35) : 4595 - 4597
  • [35] Enantioselective iridium-catalyzed allylic amination of ammonia and convenient ammonia surrogates
    Pouy, Mark J.
    Leitner, Andreas
    Weix, Daniel J.
    Ueno, Satoshi
    Hartwig, John F.
    ORGANIC LETTERS, 2007, 9 (20) : 3949 - 3952
  • [36] Iridium-catalyzed enantioselective alkynylation and kinetic resolution of alkyl allylic alcohols
    Guo, Jia
    Ma, Hao-Ran
    Xiong, Wen-Bin
    Fan, Luoyi
    Zhou, You-Yun
    Wong, Henry N. C.
    Cui, Jian-Fang
    CHEMICAL SCIENCE, 2022, 13 (46) : 13914 - 13921
  • [37] Enantioselective Synthesis of Tetrahydroisoquinolines via Iridium-Catalyzed Intramolecular Friedel-Crafts-Type Allylic Alkylation of Phenols
    Xu, Qing-Long
    Dai, Li-Xin
    You, Shu-Li
    ORGANIC LETTERS, 2012, 14 (10) : 2579 - 2581
  • [38] Iridium-Catalyzed Enantioselective Allylic Alkylation of Methyl 2-(4-nitrophenylsulfonyl)acetate and Subsequent Transformations
    Xu, Qing-Long
    Dai, Li-Xin
    You, Shu-Li
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (11-12) : 2275 - 2282
  • [39] Iridium-catalyzed enantioselective allylic substitutions with aliphatic nitro compounds as prenucleophiles
    Dahnz, A
    Helmchen, G
    SYNLETT, 2006, (05) : 697 - 700
  • [40] Iridium-Catalyzed Enantioselective Allylic Substitution of O-Allyl Carbamothioates
    Xu, Qing-Long
    Liu, Wen-Bo
    Dai, Li-Xin
    You, Shu-Li
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (13): : 4615 - 4618
12345