Optically Pure C1-Symmetric Cyclic(alkyl)(amino)carbene Ruthenium Complexes for Asymmetric Olefin Metathesis

被引：31

作者：

Morvan, Jennifer ^{[1
]}

Vermersch, Francois ^{[2
]}

Zhang, Ziyun ^{[3
]}

Falivene, Laura ^{[4
]}

Vives, Thomas ^{[1
]}

Dorcet, Vincent ^{[1
]}

Roisnel, Thierry ^{[1
]}

Crevisy, Christophe ^{[1
]}

Cavallo, Luigi ^{[3
]}

Vanthuyne, Nicolas ^{[5
]}

Bertrand, Guy ^{[2
]}

Jazzar, Rodolphe ^{[2
]}

Mauduit, Marc ^{[1
]}

机构：

[1] Univ Rennes, CNRS, Ecole Natl Super Chim Rennes, ISCR UMR 6226, F-35000 Rennes, France

[2] Univ Calif San Diego, Dept Chem & Biochem, UCSD CNRS Joint Res Chem Lab UMI 3555, La Jolla, CA 92093 USA

[3] King Abdullah Univ Sci & Technol KAUST, KAUST Catalysis Ctr KCC, Thuwal 239556900, Saudi Arabia

[4] Univ Salerno, Dipartimento Chim & Biol, I-84100 Fisiciano, Italy

[5] Aix Marseille Univ, CNRS, F-13397 Marseille, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 47期

关键词：

N-HETEROCYCLIC CARBENES; CYCLIC (ALKYL)(AMINO)CARBENES CAACS; CATALYSTS; MECHANISM; BEARING; LIGANDS; REACTIVITY;

D O I：

10.1021/jacs.0c10705

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An expedient access to the first optically pure ruthenium complexes containing C-1-symmetric cyclic (alkyl)(amino)carbene ligands is reported. They demonstrate excellent catalytic performances in asymmetric olefin metathesis with high enantioselectivities (up to 92% ee). Preliminary mechanistic insights provided by density functional theory models highlight the origin of the enantioselectivity.

引用

页码：19895 / 19901

页数：7

共 28 条

[1] Cyclic(alkyl)(amino)carbene ruthenium complexes for Z-stereoselective (asymmetric) olefin metathesis
Morvan, Jennifer
Vermersch, Francois
Lorkowski, Jan
Talcik, Jakub
Vives, Thomas
Roisnel, Thierry
Crevisy, Christophe
Vanthuyne, Nicolas
Bertrand, Guy
Jazzar, Rodolphe
Mauduit, Marc
CATALYSIS SCIENCE & TECHNOLOGY, 2023, 13 (02) : 381 - 388
[2] Bis(Cyclic Alkyl Amino Carbene) Ruthenium Complexes: AVersatile, Highly Efficient Tool for Olefin Metathesis
Gawin, Rafal
Kozakiewicz, Anna
Gunka, Piotr A.
Dabrowski, Pawel
Skowerski, Krzysztof
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (04) : 981 - 986
[3] Highly Robust and Efficient Blechert-Type Cyclic(alkyl)(amino)carbene Ruthenium Complexes for Olefin Metathesis
Del Vecchio, Antonio
Talcik, Jakub
Colombel-Rouen, Sophie
Lorkowski, Jan
Serrato, Melinda R.
Roisnel, Thierry
Vanthuyne, Nicolas
Bertrand, Guy
Jazzar, Rodolphe
Mauduit, Marc
ACS CATALYSIS, 2023, 13 (09) : 6195 - 6202
[4] Synthesis and Activity of Six-Membered Cyclic Alkyl Amino Carbene-Ruthenium Olefin Metathesis Catalysts
Samkian, Adrian E.
Xu, Yan
Virgil, Scott C.
Yoon, Ki-Young
Grubbs, Robert H.
ORGANOMETALLICS, 2020, 39 (04) : 495 - 499
[5] Neutral and Cationic Molybdenum Imido Alkylidene Cyclic Alkyl Amino Carbene (CAAC) Complexes for Olefin Metathesis
Kundu, Koushani
Musso, Janis V.
Benedikter, Mathis J.
Frey, Wolfgang
Gugeler, Katrin
Kaestner, Johannes
Buchmeiser, Michael R.
CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (52)
[6] Group 1 and 2 cyclic (alkyl)(amino) carbene complexes
Turner, Zoe R.
Buffet, Jean-Charles
DALTON TRANSACTIONS, 2015, 44 (29) : 12985 - 12989
[7] Synthesis and catalytic olefin metathesis activity of amberlyst-15 supported cyclic and bicyclic alkyl amino carbene ruthenium complexes
Deme, Janos
Nagyhazi, Marton
May, Zoltan
Hancsok, Jeno
Valyon, Jozsef
Keki, Sandor
Tuba, Robert
Turczel, Gabor
REACTION KINETICS MECHANISMS AND CATALYSIS, 2022, 135 (05) : 2519 - 2531
[8] Ambivalent Role of Rotamers in Cyclic(alkyl)(amino)carbene Ruthenium Complexes for Enantioselective Ring-Opening Cross- Metathesis
Morvan, Jennifer
Vermersch, Francois
Zhang, Ziyun
Vives, Thomas
Roisnel, Thierry
Crevisy, Christophe
Falivene, Laura
Cavallo, Luigi
Vanthuyne, Nicolas
Bertrand, Guy
Jazzar, Rodolphe
Mauduit, Marc
ORGANOMETALLICS, 2023, 42 (06) : 495 - 504
[9] Ambivalent Role of Rotamers in Cyclic(alkyl)(amino)carbene Ruthenium Complexes for Enantioselective Ring-Opening Cross-Metathesis
Morvan, Jennifer
Vermersch, Francois
Zhang, Ziyun
Vives, Thomas
Roisnel, Thierry
Crevisy, Christophe
Falivene, Laura
Cavallo, Luigi
Vanthuyne, Nicolas
Bertrand, Guy
Jazzar, Rodolphe
Mauduit, Marc
ORGANOMETALLICS, 2023,
[10] Air and Thermally Stable Cyclic (Alkyl)(amino)carbene Ruthenium Complexes for Efficient Ring Expansion Metathesis Polymerization
Jang, Minjae
Jung, Eunsong
Yang, Yongkang
Noh, Jinkyung
Song, Hayoung
Kim, Hyunseok
Kang, Hoonseok
Choe, Solhye
Choi, Tae-Lim
Lee, Eunsung
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (03) : 2571 - 2578

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