Asymmetric Synthesis of α-Alkylated Aldehydes using Terminal Epoxide-Derived Chiral Enamines

被引:25
|
作者
Hodgson, David M. [1 ]
Kaka, Naeem S. [1 ]
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
基金
英国工程与自然科学研究理事会;
关键词
aldehydes; alkylation; asymmetric synthesis; enamines; terminal epoxides;
D O I
10.1002/anie.200804369
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Effective discrimination: Efficient lithium amide-induced terminal epoxide-enamine transformation provides the first enamines capable of generating α-alkylated aldehydes with high asymmetric induction by intermolecular nucleophilic substitution (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9958 / 9960
页数:3
相关论文
共 50 条
  • [1] Enantioselective Synthesis of Chiral Tetrahydroisoquinolines by Iridium-Catalyzed Asymmetric Hydrogenation of Enamines
    Yan, Pu-Cha
    Xie, Jian-Hua
    Hou, Guo-Hua
    Wang, Li-Xin
    Zhou, Qi-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3243 - 3250
  • [2] Asymmetric cyanohydrin synthesis from aldehydes and ketones using chiral metal (salen) complex as catalyst
    Kim, Sung Soo
    PURE AND APPLIED CHEMISTRY, 2006, 78 (05) : 977 - 983
  • [3] L-Alanine-derived Chiral Ligands for Asymmetric Addition of Diethylzinc to Aldehydes
    Kang, Seock Yong
    Baek, Jinho
    Kang, Kyoung Hee
    Lee, Jeong-ae
    Park, Yong Sun
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (09): : 3125 - 3128
  • [4] Asymmetric Synthesis of Chiral Oxazolines by Organocatalytic Cyclization of α-Aryl Isocyanoesters with Aldehydes
    Xue, Meng-Xia
    Guo, Chang
    Gong, Liu-Zhu
    SYNLETT, 2009, (13) : 2191 - 2197
  • [5] Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts
    Gupta, Anil K.
    Yin, Xiaopeng
    Mukherjee, Munmun
    Desai, Aman A.
    Mohammadlou, Aliakbar
    Jurewicz, Kelsee
    Wulff, William D.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (11) : 3361 - 3367
  • [6] Synthesis of chiral β-amino acid derivatives by asymmetric hydrosilylation with an imidazole derived organocatalyst
    Jones, Simon
    Li, Xianfu
    TETRAHEDRON, 2012, 68 (27-28) : 5522 - 5532
  • [7] Asymmetric synthesis of chiral aldehydes by conjugate additions with bifunctional organocatalysis by cinchona alkaloids
    Wu, Fanghui
    Hong, Ran
    Khan, Jihan
    Liu, Xiaofeng
    Deng, Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4301 - 4305
  • [8] Synthesis of Recyclable Fluorous Chiral Ligands and Evaluation of Their Catalytic Activity toward Asymmetric Addition of Dimethylzinc to Aldehydes
    Sokeirik, Yasser S.
    Hoshina, Akiko
    Omote, Masaaki
    Sato, Kazuyuki
    Tarui, Atsushi
    Kumadaki, Itsumaro
    Ando, Akira
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (10) : 1850 - 1856
  • [9] Enantioselective Synthesis of Chiral β-Aryloxy Alcohols by Asymmetric Hydrogenation of α-Aryloxy Aldehydes via Dynamic Kinetic Resolution
    Zhou, Zhang-Tao
    Xie, Jian-Hua
    Zhou, Qi-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (03) : 363 - 366
  • [10] Synthesis of γ-amino alcohols from aldehydes, enamines, and trichlorosilane using Lewis base catalysts
    Kashiwagi, Takeru
    Kotani, Shunsuke
    Sugiura, Masaharu
    Nakajima, Makoto
    TETRAHEDRON, 2011, 67 (02) : 531 - 539