Synthesis of bornene-2,2′-diamino-1,1′-binaphthalene conjugates in palladium-catalysed aminocarbonylations

被引：13
|
作者：
Mikle, Gabor [1 ,2 ]
Boros, Borbala [3 ]
Kollar, Laszlo [1 ,2 ,4 ]
机构：
[1] Univ Pecs, Dept Inorgan Chem, POB 266, H-7624 Pecs, Hungary
[2] Szentagothai Res Ctr, POB 266, H-7624 Pecs, Hungary
[3] Univ Pecs, Dept Analyt & Environm Chem, Ifjusag U 6, H-7624 Pecs, Hungary
[4] MTA PTE Res Grp Select Chem Synth, Ifjusag U 6, H-7624 Pecs, Hungary
来源：
TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 9-10期
基金：
匈牙利科学研究基金会;
关键词：
CARBONYLATION; ARYL; IODOALKENE; RESOLUTION; COMPLEXES; MECHANISM;
D O I：
10.1016/j.tetasy.2016.03.010
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Palladium-catalysed aminocarbonylation of a terpenoic iodoalkene (2-iodo-bornene) model compound with both enantiomerically pure and racemic 2,2'-diamino-1,1'-binaphthalene (BINAM) as the N-nucleophile was carried out. All of the diastereoisomers of the monocarboxamide (N-bornenyl carboxamide) and dicarboxamide (N,N'-dinorbomenylcarboxamide) derivatives were synthesised. The diastereoselectivities of the aminocarbonylation were investigated in both cases: either racemic BINAM was used as the N-nucleophile in the aminocarbonylation of enantiomerically pure 2-iodobornene or racemic iodobornene was aminocarbonylated with enantiomerically pure BINAM with moderate diastereoselectivities. In this way, all possible diastereoisomers of binaphthalene-bornene conjugates were synthesised in moderate to high yields by asymmetric (diastereoselective) aminocarbonylation. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：377 / 383
页数：7
相关论文
共 50 条
  • [1] Diastereoselective aminocarbonylation of a steroidal iodoalkene with 2,2′-diamino-1,1′-binaphthalene in palladium-catalysed reactions
    Mikle, Gabor
    Boros, Borbala
    Kollar, Laszlo
    TETRAHEDRON-ASYMMETRY, 2014, 25 (23) : 1527 - 1531
  • [2] Preparation and application in asymmetrical synthesis of 2,2′-diamino-1,1′-binaphthalene
    Zhang, ZH
    Mo, LP
    Liu, QB
    Li, TS
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2003, 23 (01) : 37 - 43
  • [3] Preparation of Optically Active Polyimides Based on 2,2′-diamino-1,1′-binaphthalene
    Sysel, Petr
    Holakovsky, Roman
    Hovorka, Stepan
    Zadny, Jaroslav
    Izak, Pavel
    JOURNAL OF POLYMER MATERIALS, 2022, 39 (3-4): : 325 - 335
  • [4] Synthesis of Axially Chiral Carboxamides via Aminocarbonylation of Aryl and Vinyl Iodides with 2,2'-Diamino-1,1'-binaphthalene in the Presence of Palladium Catalysts
    Palinkas, Noemi
    Mikle, Gabor
    Aranyi, Anita
    Peter, Antal
    Kollar, Laszlo
    CHEMISTRYSELECT, 2020, 5 (35): : 11048 - 11051
  • [5] A new approach to the synthesis of 2,2′-diamino-1,1′-binaphthyl
    Tan, DM
    Wu, JA
    Wang, B
    Xu, ZL
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2001, 21 (01) : 64 - 65
  • [6] The interaction of R(+)- or S(-)-2,2′-diamino-1,1′-binaphthalene with a Pd/silica catalyst in tetrahydrofuran
    Jackson, SD
    Robinson, GE
    Webb, G
    Young, NC
    ENANTIOMER, 2000, 5 (06): : 567 - 570
  • [7] N,N′-Diaryl derivatives of (S)-2,2′-diamino-1,1′-binaphthalene for fluorescent enantioselective detection
    Malysheva, A. S.
    Averin, A. D.
    Beletskaya, I. P.
    RUSSIAN CHEMICAL BULLETIN, 2024, 73 (07) : 1944 - 1952
  • [8] Reactivity of triosmium and triruthenium carbonyls with 2,2′-diamino-1,1′-binaphthalene.: Synthesis of C- and N-metalated derivatives
    Cabeza, JA
    da Silva, I
    del Río, I
    García-Granda, S
    Riera, V
    Sánchez-Vega, MG
    ORGANOMETALLICS, 2003, 22 (07) : 1519 - 1525
  • [9] Photosubstitution of dichloro(2,2′-diamino-1,1′-binaphthyl)platinum(II)
    Kunkely, H
    Vogler, A
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1998, 114 (03) : 193 - 195
  • [10] Acid-catalyzed condensation of 2,2′-diamino-1,1′-biaryls for the synthesis of benzo[c]carbazoles
    Lim, Byong-Yun
    Choi, Min-Kyung
    Cho, Cheon-Gyu
    TETRAHEDRON LETTERS, 2011, 52 (45) : 6015 - 6017
12345