Bis-Sulfamyl Imines: Potent Substrates for Asymmetric Additions of Arylboroxines under Rhodium Catalysis

被引：26
作者：
Crampton, Rosemary [1 ]
Woodward, Simon [1 ]
Fox, Martin [2 ]
机构：
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] Chirotech Technol Ltd, Cambridge CB4 0GH, England
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 06期
基金：
英国工程与自然科学研究理事会;
关键词：
asymmetric catalysis; boron; diarylmethylamines; protecting groups; rhodium; N-TOSYLARYLIMINES; ARYLATION; AMINES; LIGAND; REAGENTS; ACIDS; MILD;
D O I：
10.1002/adsc.201000838
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Bis-sulfamyl imines are shown to be potentially ideal substrates for rhodium-catalysed asymmetric additions of arylboron nucleophiles as they show: (i) near perfect enantioselectivities (11 examples, 98-99+% ee), (ii) good to excellent diastereoselectivities (10-32:1 rac:meso), and (iii) high functional group tolerance in removal of the low molecular weight protecting group via mild heating in aqueous pyridine.
引用
收藏
页码：903 / 906
页数：4
相关论文
共 27 条
  • [1] Mild and safer preparative method for nonsymmetrical sulfamides via N-sulfamoyloxazolidinone derivatives:: Electronic effects affect the transsulfamoylation reactivity
    Borghese, A.
    Antoine, L.
    Van Hoeck, J. P.
    Mockel, A.
    Merschaert, A.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (04) : 770 - 775
  • [2] Development of Binaphthyl-Based Chiral Dienes for Rhodium(I)-Catalyzed Asymmetric Arylation of N,N-Dimethylsulfamoyl-Protected Aldimines
    Cao, Ziping
    Du, Haifeng
    [J]. ORGANIC LETTERS, 2010, 12 (11) : 2602 - 2605
  • [3] A NEW SYNTHESIS OF PRIMARY AMINES FROM DIARYLIDENESULFAMIDES
    DAVIS, FA
    GIANGIORDANO, MA
    STARNER, WE
    [J]. TETRAHEDRON LETTERS, 1986, 27 (34) : 3957 - 3960
  • [4] Enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids
    Duan, Hai-Feng
    Jia, Yi-Xia
    Wang, Li-Xin
    Zhou, Qi-Lin
    [J]. ORGANIC LETTERS, 2006, 8 (12) : 2567 - 2569
  • [5] Binding characteristics of cetirizine and levocetirizine to human H1 histamine receptors:: Contribution of Lys191 and Thr194
    Gillard, M
    Van Der Perren, C
    Moguilevsky, N
    Massingham, R
    Chatelain, P
    [J]. MOLECULAR PHARMACOLOGY, 2002, 61 (02) : 391 - 399
  • [6] Steric Tuning of the Amidomonophosphane-Rhodium(I) Catalyst in Asymmetric Addition of Arylboroxines to N-Phosphinoyl Aldimines
    Hao, Xinyu
    Kuriyama, Masami
    Chen, Qian
    Yamamoto, Yasutomo
    Yamada, Ken-ichi
    Tomioka, Kiyoshi
    [J]. ORGANIC LETTERS, 2009, 11 (19) : 4470 - 4473
  • [7] Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines
    Hayashi, T
    Kawai, M
    Tokunaga, N
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) : 6125 - 6128
  • [8] Rhodium-catalyzed asymmetric arylation of imines with organostannanes. Asymmetric synthesis of diarylmethylamines
    Hayashi, T
    Ishigedani, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (05) : 976 - 977
  • [9] Hayashi T., 2004, Angew. Chem, V116, P6251, DOI DOI 10.1002/ANGE.200461338
  • [10] Hermanns N, 2002, ANGEW CHEM INT EDIT, V41, P3692, DOI 10.1002/1521-3773(20021004)41:19<3692::AID-ANIE3692>3.0.CO
123