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
  • [41] Iridium-Catalyzed Diastereoselective and Enantioselective Allylic Substitutions with Acyclic -Alkoxy Ketones
    Jiang, Xingyu
    Chen, Wenyong
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (19) : 5819 - 5823
  • [42] Iridium-catalyzed enantioselective synthesis of allylic alcohols: Silanolates as hydroxide equivalents
    Lyothier, Isabelle
    Defieber, Christian
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (37) : 6204 - 6207
  • [43] Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols
    Ueno, Satoshi
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1928 - 1931
  • [44] Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides
    López, F
    Ohmura, T
    Hartwig, JF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) : 3426 - 3427
  • [45] Highly Enantioselective Synthesis of Tetrahydrocarbolines via Iridium-Catalyzed Intramolecular Friedel-Crafts Type Allylic Alkylation Reactions
    Xu, Qing-Long
    Zhuo, Chun-Xiang
    Dai, Li-Xin
    You, Shu-Li
    ORGANIC LETTERS, 2013, 15 (23) : 5909 - 5911
  • [46] Iridium-catalyzed regio- and enantioselective allylic esterification of secondary allylic alcohols with carboxylic acids
    Tang, Shengbiao
    Zhang, Peng
    Wang, Changkai
    Shao, Ying
    Sun, Jiangtao
    CHEMICAL COMMUNICATIONS, 2021, 57 (84) : 11080 - 11083
  • [47] Stereodivergent synthesis via iridium-catalyzed asymmetric double allylic alkylation of cyanoacetate
    Shen, Chong
    Cheng, Xiang
    Wei, Liang
    Wang, Ruo-Qing
    Wang, Chun-Jiang
    CHEMICAL SCIENCE, 2021, 12 (48) : 15882 - 15891
  • [48] Iridium-Catalyzed Asymmetric Allylic Substitutions
    Liu, Wen-Bo
    Xia, Ji-Bao
    You, Shu-Li
    TRANSITION METAL CATALYZED ENANTIOSELECTIVE ALLYLIC SUBSTITUTION IN ORGANIC SYNTHESIS, 2012, 38 : 155 - 207
  • [49] Iridium-Catalyzed Allylic Fluorination of Trichloroacetimidates
    Topczewski, Joseph J.
    Tewson, Timothy J.
    Nguyen, Hien M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (48) : 19318 - 19321
  • [50] Iridium-Catalyzed, Regio- and Enantioselective Allylic Substitution with Aromatic and Aliphatic Sulfinates
    Ueda, Mitsuhiro
    Hartwig, John F.
    ORGANIC LETTERS, 2010, 12 (01) : 92 - 94
12345