Asymmetric hydrosilylations of N-sulfonyl ketimines and vicinal diimines with chiral boranes

被引:2
|
作者
Liu, Ting [1 ,2 ]
Feng, Xiangqing [1 ,2 ]
Du, Haifeng [1 ,2 ]
机构
[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
Asymmetric hydrosilylation; N -Sulfonyl ketimines; Vicinal diimines; Chiral boranes; FLPs; FRUSTRATED LEWIS PAIRS; METAL-FREE HYDROGENATION; B(C6F5)(3)-CATALYZED HYDROSILYLATION; ENANTIOSELECTIVE SYNTHESIS; MECHANISM; HYDROSILATION; AUXILIARIES; CHEMISTRY;
D O I
10.1016/j.tetlet.2022.154202
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free hydrosilylation of N-sulfonyl ketimines under the FLP catalysis has been realized to give optically active amines in high yields with up to 73% ee. Significantly, a chiral borane-catalyzed asymmet-ric hydrosilylation of vicinal diimines was also achieved, affording the desired cis-1,2-diamines with 12- 70% ee's.(c) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 25 条
  • [1] Asymmetric Synthesis of (Triaryl)methylamines by Rhodium-Catalyzed Addition of Arylboroxines to Cyclic N-Sulfonyl Ketimines
    Nishimura, Takahiro
    Noishiki, Akira
    Tsui, Gavin Chit
    Hayashi, Tamio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) : 5056 - 5059
  • [2] B(C6F5)3-Catalyzed Reduction of Cyclic N-Sulfonyl Ketimines
    Shi, Lei
    Bao, Robert Li-Yuan
    Zheng, Limin
    Zhao, Rong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (38) : 6550 - 6556
  • [3] Rhodium-Catalyzed Direct ortho C-H Thiolation of Cyclic N-Sulfonyl Ketimines
    Shi, Guangrui
    Khan, Ruhima
    Zhang, Xuexin
    Yang, Yong
    Zhan, Yong
    Li, Juan
    Luo, Yang
    Fan, Baomin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (05) : 788 - 792
  • [4] Asymmetric Alkynylation of Cyclic N-Sulfonyl Imines using Synergistic Chiral Phosphoric Acid/Copper Catalysis
    Li, Ya-Ling
    Liu, Jin-Xin
    Chen, Xiao-Pan
    Zhou, Yuan
    Xiao, You-Cai
    Chen, Fen-Er
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (15) : 3202 - 3207
  • [5] Rhodium-catalyzed [2+2+2] cycloaddition reactions of terminal alkynes with N-sulfonyl ketimines
    Zhang, Wei
    Zhang, Qian-Ru
    Dong, Lin
    TETRAHEDRON LETTERS, 2015, 56 (03) : 546 - 548
  • [6] N-Sulfonyl α-imino ester-derived chiral oxaziridines: catalytic asymmetric synthesis and application as a modular chiral organic oxidant
    Tanaka, Naoya
    Tsutsumi, Ryosuke
    Uraguchi, Daisuke
    Ooi, Takashi
    CHEMICAL COMMUNICATIONS, 2017, 53 (52) : 6999 - 7002
  • [7] Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines
    Gutierrez, David A.
    Fettinger, James
    Houk, K. N.
    Ando, Kaori
    Shaw, Jared T.
    ORGANIC LETTERS, 2022, 24 (05) : 1164 - 1168
  • [8] Rhodium-catalyzed asymmetric addition of arylboronic acids to cyclic N-sulfonyl ketimines towards the synthesis of α,α-diaryl-α-amino acid derivatives
    Takechi, Ryosuke
    Nishimura, Takahiro
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (17) : 4918 - 4924
  • [9] Asymmetric construction of enantioenriched spiro gem-diamines via [3+3] annulation of α,β-unsaturated N-sulfonyl ketimines and 3-aminobenzofurans
    Shu, Xin
    Zhang, Tingting
    Zhang, Yongxing
    Tong, Kexin
    Wang, Shumin
    Wang, Yang
    ORGANIC CHEMISTRY FRONTIERS, 2025,
  • [10] Asymmetric Organocatalytic Aza-Friedel-Crafts Reaction of Naphthols with N-Sulfonyl Imines
    Chauhan, Pankaj
    Chimni, Swapandeep Singh
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (09) : 1636 - 1640