Recent Developments in Asymmetric Nazarov Reactions

被引:0
|
作者
Pellissier, Helene [1 ]
机构
[1] Aix Marseille Univ, CNRS, Cent Marseille, iSM2, Marseille, France
关键词
Asymmetric Nazarov reactions; asymmetric cyclizations; chiral auxiliaries; chiral catalysts; asymmetric catalysis; chirality; domino reactions; ENANTIOSELECTIVE SYNTHESIS; ELECTROCYCLIC REACTIONS; DOMINO REACTIONS; CYCLIZATION; CASCADE; ACID; ORGANOCATALYSIS; INTERMEDIATE; STRATEGY; TRENDS;
D O I
10.2174/0113852728296619240321060646
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Nazarov reaction involves the cyclization of divinyl ketones into cyclopentenones under the influence of strong acids. The prevalence of five-membered carbocycles in a multitude of natural and bioactive products has triggered an intense development of efficient methods for their construction. In particular, asymmetric versions of the Nazarov reaction are achieved by using either a chiral auxiliary or a chiral catalyst, which can be an organocatalyst, a metal catalyst, or a multicatalytic system. This review aims to update the field of asymmetric Nazarov reactions published since 2017. It is divided into four sections, dealing successively with Nazarov reactions of chiral auxiliaries, organocatalytic enantioselective Nazarov reactions, metal/boron-catalyzed enantioselective Nazarov reactions, and multicatalytic enantioselective Nazarov reactions. Each section of the review is subdivided into simple asymmetric Nazarov reactions and Nazarov-based domino/tandem reactions, which have allowed numerous more complex functionalized chiral molecules to be synthesized in one-pot procedures.
引用
收藏
页码:757 / 776
页数:19
相关论文
共 50 条
  • [31] Developments in Organocatalytic Asymmetric Strecker Reactions
    Tang, Ranxiao
    Li, Yunpeng
    Li, Yuemin
    Liu, Weihua
    Ma, Jingjun
    Wang, Yanen
    Wang, Chun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (07) : 1048 - 1058
  • [32] A SUBSTRATE FOR THE ASYMMETRIC NAZAROV CYCLIZATION
    ANDREWS, JFP
    REGAN, AC
    WALLIS, JD
    POVEY, DC
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1992, 48 : 2196 - 2199
  • [33] An Organocatalytic Asymmetric Nazarov Cyclization
    Basak, Ashok K.
    Shimada, Naoyuki
    Bow, William F.
    Vicic, David A.
    Tius, Marcus A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) : 8266 - +
  • [34] Binaphthyl Based Molecules for Asymmetric Organocatalytic Aldol Reactions: Recent Developments from a Successful Record
    Almeida, Ana R.
    Neves, Angela C. B.
    Abreu, Artur R.
    Calvete, Mario J. F.
    Pereira, Mariette M.
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2014, 11 (02) : 129 - 140
  • [35] Recent trends and developments in the asymmetric synthesis of profens
    Wang, Qiuyue
    Qi, Yuchen
    Gao, Xuefeng
    Gong, Lili
    Wan, Ruiying
    Lei, Weihua
    Wang, Zhenguo
    Mao, Jianyou
    Guan, Haixing
    Li, Wei
    Walsh, Patrick J.
    GREEN SYNTHESIS AND CATALYSIS, 2023, 4 (02): : 89 - 103
  • [36] Recent developments in asymmetric reduction of ketones with biocatalysts
    Nakamura, K
    Yamanaka, R
    Matsuda, T
    Harada, T
    TETRAHEDRON-ASYMMETRY, 2003, 14 (18) : 2659 - 2681
  • [37] Recent developments in the area of asymmetric transfer hydrogenation
    Wills, M
    Palmer, M
    Smith, A
    Kenny, J
    Walsgrove, T
    MOLECULES, 2000, 5 (01) : 4 - 18
  • [38] Recent Developments and Perspectives in the Asymmetric Mannich Reaction
    Saranya, Salim
    Harry, Nissy Ann
    Krishnan, K. Keerthi
    Anilkumar, Gopinathan
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (04) : 613 - 633
  • [39] Asymmetric Hydroamination: A Survey of the Most Recent Developments
    Hannedouche, Jerome
    Schulz, Emmanuelle
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (16) : 4972 - 4985
  • [40] Catalytic asymmetric synthesis of spirooxindoles: recent developments
    Mei, Guang-Jian
    Shi, Feng
    CHEMICAL COMMUNICATIONS, 2018, 54 (50) : 6607 - 6621