Synthesis of new ferrocenyl-containing tertiary alcohols, analogs of l-prolinol-based organocatalysts

被引:1
作者
Burlutsky, Roman O. [1 ]
Yudina, Ella S. [1 ]
Churakov, Andrei, V [2 ]
Lemenovskiy, Dmitriy A. [1 ]
Dyadchenko, Victor P. [1 ]
机构
[1] M V Lomonosov Moscow State Univ, Dept Chem, Moscow 119991, Russia
[2] Russian Acad Sci, N S Kurnakov Inst Gen & Inorgan Chem, Moscow 119991, Russia
关键词
asymmetric organocatalysis; ferrocene; proline; tert-butoxycarbonyl protective group; ferrocenylmagnesium bromide; chiral tertiary alcohols; X-ray molecular structure; ENANTIOSELECTIVE SYNTHESIS; DERIVATIVES; CATALYSTS;
D O I
10.1016/j.mencom.2024.01.019
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Syntheses of new ferrocenyl-containing tertiary alcohols derived from l-proline were developed. In these alcohols, two ferrocenyl groups are bonded at prolinol moiety directly or through p-phenylene spacer. Specific features for the ferrocene Grignard reagents were discovered.
引用
收藏
页码:64 / 66
页数:3
相关论文
共 19 条
[1]   Asymmetric Aldol "Reaction in Water" Using Ferrocene-Amino Acid Conjugates [J].
Al-Momani, Lo'ay ;
Lataifeh, Anas .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2022, 61 (06) :2417-2424
[2]   Attempts to mimic key bond-forming events associated with the proposed biogenesis of the pentacyclic lamellarins [J].
Axford, Lorraine C. ;
Holden, Kate E. ;
Hasse, Katrin ;
Banwell, Martin G. ;
Steglich, Wolfgang ;
Wagler, Jorg ;
Willis, Anthony C. .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2008, 61 (02) :80-93
[3]   Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives [J].
Bonsignore, Martina ;
Benaglia, Maurizio ;
Raimondi, Laura ;
Orlandi, Manuel ;
Celentano, Giuseppe .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :633-640
[4]   Nucleophilic chiral amines as catalysts in asymmetric synthesis [J].
France, S ;
Guerin, DJ ;
Miller, SJ ;
Lectka, T .
CHEMICAL REVIEWS, 2003, 103 (08) :2985-3012
[5]   Supported proline and proline-derivatives as recyclable organocatalysts [J].
Gruttadauria, Michelangelo ;
Giacalone, Francesco ;
Noto, Renato .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (08) :1666-1688
[6]   Remote chirality transfer in nucleophilic catalysis with N-(4-pyridinyl)-L-proline derivatives [J].
Kawabata, T ;
Stragies, R ;
Fukaya, T ;
Fuji, K .
CHIRALITY, 2003, 15 (01) :71-76
[7]   Asymmetric aldol reactions in ketone/ketone systems catalyzed by ionic liquid-supported C2-symmetrical organocatalyst [J].
Kochetkov, Sergei V. ;
Kucherenko, Alexander S. ;
Zlotin, Sergei G. .
MENDELEEV COMMUNICATIONS, 2015, 25 (03) :168-170
[8]   Green Asymmetric Organocatalysis [J].
Kristofikova, Dominika ;
Modrocka, Viktoria ;
Meciarova, Maria ;
Sebesta, Radovan .
CHEMSUSCHEM, 2020, 13 (11) :2828-2858
[9]   Asymmetric organocatalysis: from proline to highly efficient immobilized organocatalysts [J].
Kucherenko, A. S. ;
Siyutkin, D. E. ;
Maltsev, O. V. ;
Kochetkov, S. V. ;
Zlotin, S. G. .
RUSSIAN CHEMICAL BULLETIN, 2012, 61 (07) :1313-1320
[10]   The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols [J].
List, B ;
Pojarliev, P ;
Biller, WT ;
Martin, HJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :827-833