Construction of Quaternary Stereogenic Carbon Centers through Copper-Catalyzed Enantioselective Allylic Alkylation of Azoles

被引:51
|
作者
Ohmiya, Hirohisa [1 ]
Zhang, Heng [1 ]
Shibata, Saori [1 ]
Harada, Ayumi [1 ]
Sawamura, Masaya [1 ]
机构
[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
关键词
allylic compounds; asymmetric catalysis; carbenes; copper; heterocycles; FRIEDEL-CRAFTS ALKYLATION; CONJUGATE ADDITION; SUBSTITUTION; REAGENTS; ALKENES; STEREOCENTERS; INDOLES; TERTIARY; IMINES; BONDS;
D O I
10.1002/anie.201600619
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Copper-catalyzed enantioselective allylic alkylation of azoles with ,-disubstituted primary allylic phosphates was achieved using a new chiral N-heterocyclic carbene ligand bearing a naphtholic hydroxy group. This reaction occurred with excellent branch regioselectivity and high enantioselectivity, thus forming a controlled all-carbon quaternary stereogenic center at the position to the heteroaromatic ring.
引用
收藏
页码:4777 / 4780
页数:4
相关论文
共 50 条
  • [41] Insights into the Mechanism of Enantioselective Copper-Catalyzed Ring-Opening Allylic Alkylation of Cyclopropanols
    Kitabayashi, Akito
    Mizushima, Sho
    Higashida, Kosuke
    Yasuda, Yuto
    Shimizu, Yohei
    Sawamura, Masaya
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (11) : 1855 - 1862
  • [42] Enantioselective Pd-Catalyzed Decarboxylative Allylic Alkylation of Thiopyranones. Access to Acyclic, Stereogenic α-Quaternary Ketones
    Alexy, Eric J.
    Virgil, Scott C.
    Bartberger, Michael D.
    Stoltz, Brian M.
    ORGANIC LETTERS, 2017, 19 (19) : 5007 - 5009
  • [43] Copper-Catalyzed Asymmetric Propargylic Alkylation with Oxindoles: Diastereo- and Enantioselective Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters
    Xia, Jin-Tao
    Hu, Xiang-Ping
    ORGANIC LETTERS, 2020, 22 (03) : 1102 - 1107
  • [44] Enantioselective Construction of All-Carbon Quaternary Stereogenic Centers by Using Phosphine Catalysis
    Li, Huilin
    Lu, Yixin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (09) : 1130 - 1145
  • [45] ENANTIOSELECTIVE CONSTRUCTION OF QUATERNARY STEREOGENIC CENTERS POSSESSING A FLUORINE ATOM
    IHARA, M
    TANIGUCHI, N
    KAI, T
    SATOH, K
    FUKUMOTO, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (02): : 221 - 227
  • [46] Progress in Copper-Catalyzed Asymmetric Allylic Alkylation Reaction
    Cui, Penglei
    Liu, Haiyan
    Zhang, Dongnuan
    Wang, Chun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (08) : 1401 - 1409
  • [48] Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation
    Reeves, Corey M.
    Eidamshaus, Christian
    Kim, Jimin
    Stoltz, Brian M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (26) : 6718 - 6721
  • [49] Copper-Catalyzed Asymmetric Allylic Alkylation of -Keto Esters with Allylic Alcohols
    Trillo, Paz
    Baeza, Alejandro
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) : 1735 - 1741
  • [50] Enantioselective Construction of Vicinal Quaternary- Tetrasubstituted Carbon Stereocenters by Copper-Catalyzed Decarboxylative Propargylic Substitution
    You, Yong
    Li, Ting-Ting
    Sun, Ting-Jia
    Zhang, Yan-Ping
    Wang, Zhen-Hua
    Zhao, Jian-Qiang
    Yuan, Wei-Cheng
    ORGANIC LETTERS, 2022, 24 (41) : 7671 - 7676