Synthesis, structure and catalytic activity of new ferrocenyl-containing secondary alcohols derived from l-proline

被引:0
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] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia
[2] Russian Acad Sci, NS Kurnakov Inst Gen & Inorgan Chem, Moscow 119991, Russia
关键词
asymmetric organocatalysis; ferrocene; proline; benzyloxycarbonyl protective group; ferrocenylmagnesium bromide; chiral secondary alcohols; X-ray molecular structure; enantioselective addition; diethylzinc; ENANTIOSELECTIVE SYNTHESIS; ORGANOCATALYSIS; DERIVATIVES;
D O I
10.1016/j.mencom.2024.02.013
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New ferrocenyl-containing diastereomeric secondary alcohols derived from L-proline of (ferrocenyl)(pyrrolidin-2-yl)methanol chemotype were synthesized. Their crystal and molecular structure was explored. The prepared chiral secondary and tertiary alcohols in which hydroxy group is sterically hindered by ferrocene substituents show asymmetric induction effect in reaction between diethylzinc and benzaldehyde.
引用
收藏
页码:201 / 203
页数:3
相关论文
共 16 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]   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
[3]   Synthesis of new ferrocenyl-containing tertiary alcohols, analogs of l-prolinol-based organocatalysts [J].
Burlutsky, Roman O. ;
Yudina, Ella S. ;
Churakov, Andrei, V ;
Lemenovskiy, Dmitriy A. ;
Dyadchenko, Victor P. .
MENDELEEV COMMUNICATIONS, 2024, 34 (01) :64-66
[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]   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
[9]   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
[10]  
Liu J, 2017, SYNTHESIS-STUTTGART, V49, P960