共 64 条
Chiral N-Heterocyclic Carbene Ligand Enabled Nickel(0)-Catalyzed Enantioselective Three-Component Couplings as Direct Access to Silylated Indanols
被引:44
作者:

Ahlin, Joachim S. E.
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech Fed Lausanne, Lab Asymmetr Catalysis & Synth, Inst Chem Sci & Engn, EPFL SB ISIC LCSA,BCH 4305, CH-1015 Lausanne, Switzerland Ecole Polytech Fed Lausanne, Lab Asymmetr Catalysis & Synth, Inst Chem Sci & Engn, EPFL SB ISIC LCSA,BCH 4305, CH-1015 Lausanne, Switzerland

Cramer, Nicolai
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech Fed Lausanne, Lab Asymmetr Catalysis & Synth, Inst Chem Sci & Engn, EPFL SB ISIC LCSA,BCH 4305, CH-1015 Lausanne, Switzerland Ecole Polytech Fed Lausanne, Lab Asymmetr Catalysis & Synth, Inst Chem Sci & Engn, EPFL SB ISIC LCSA,BCH 4305, CH-1015 Lausanne, Switzerland
机构:
[1] Ecole Polytech Fed Lausanne, Lab Asymmetr Catalysis & Synth, Inst Chem Sci & Engn, EPFL SB ISIC LCSA,BCH 4305, CH-1015 Lausanne, Switzerland
基金:
瑞士国家科学基金会;
关键词:
CATALYZED REDUCTIVE COUPLINGS;
H BOND ACTIVATION;
OLEFIN METATHESIS;
RUTHENIUM CATALYSTS;
ALLYLIC ALCOHOLS;
COLEOPHOMONE-B;
ALPHA-OLEFINS;
NHC LIGAND;
ALDEHYDES;
SILANES;
D O I:
10.1021/acs.orglett.6b01492
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
An enantioselective nickel(0)-catalyzed reductive three-component coupling between aromatic aldehydes, norbornenes, and silanes affords directly silyl-protected indanol derivatives. A new bulky chiral C-2-symmetric NHC (NHC = N-heterocyclic carbene) ligand basing on the 1,2-di(napthalen-1-yl)ethylene diamine backbone allows accessing the annulated products as single diastereoisomers in high enantioselectivity.
引用
收藏
页码:3242 / 3245
页数:4
相关论文
共 64 条
[1]
Nickel(0)-Catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled by a Chiral NHC Ligand: Efficient Access to Cyclopentenones
[J].
Ahlin, Joachim S. E.
;
Donets, Pavel A.
;
Cramer, Nicolai
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2014, 53 (48)
:13229-13233

Ahlin, Joachim S. E.
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland

Donets, Pavel A.
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland

Cramer, Nicolai
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland
[2]
Chiral N-Heterocyclic Carbene Borane Complexes: Synthesis and Structural Analysis
[J].
Banerjee, Dipshikha
;
Besnard, Celine
;
Kuendig, E. Peter
.
ORGANOMETALLICS,
2012, 31 (02)
:709-715

Banerjee, Dipshikha
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

Besnard, Celine
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

Kuendig, E. Peter
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
[3]
Highly active chiral ruthenium catalysts for asymmetric cross- and ring-opening cross metathesis
[J].
Berlin, Jacob M.
;
Goldberg, Steven D.
;
Grubbs, Robert H.
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006, 45 (45)
:7591-7595

Berlin, Jacob M.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA

Goldberg, Steven D.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA

Grubbs, Robert H.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA
[4]
Enantioselective syntheses of indanes: from organocatalysis to C-H functionalization
[J].
Borie, Cyril
;
Ackermann, Lutz
;
Nechab, Malek
.
CHEMICAL SOCIETY REVIEWS,
2016, 45 (05)
:1368-1386

Borie, Cyril
论文数: 0 引用数: 0
h-index: 0
机构:
Aix Marseille Univ, CNRS, Fac St Jerome, ICR,UMR 7273,Serv 562, 52 Ave Escadrille Niemen, F-13013 Marseille, France Aix Marseille Univ, CNRS, Fac St Jerome, ICR,UMR 7273,Serv 562, 52 Ave Escadrille Niemen, F-13013 Marseille, France

Ackermann, Lutz
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany Aix Marseille Univ, CNRS, Fac St Jerome, ICR,UMR 7273,Serv 562, 52 Ave Escadrille Niemen, F-13013 Marseille, France

Nechab, Malek
论文数: 0 引用数: 0
h-index: 0
机构:
Aix Marseille Univ, CNRS, Fac St Jerome, ICR,UMR 7273,Serv 562, 52 Ave Escadrille Niemen, F-13013 Marseille, France Aix Marseille Univ, CNRS, Fac St Jerome, ICR,UMR 7273,Serv 562, 52 Ave Escadrille Niemen, F-13013 Marseille, France
[5]
Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C-H Activation/Alkyne Insertion Reaction
[J].
Castro, Luis C. Misal
;
Obata, Atsushi
;
Aihara, Yoshinori
;
Chatani, Naoto
.
CHEMISTRY-A EUROPEAN JOURNAL,
2016, 22 (04)
:1362-1367

Castro, Luis C. Misal
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

Obata, Atsushi
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

Aihara, Yoshinori
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

论文数: 引用数:
h-index:
机构:
[6]
Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C-H Activation Reactions
[J].
Castro, Luis C. Misal
;
Chatani, Naoto
.
CHEMISTRY LETTERS,
2015, 44 (04)
:410-421

Castro, Luis C. Misal
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

论文数: 引用数:
h-index:
机构:
[7]
New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings
[J].
Chaulagain, Mani Raj
;
Sormunen, Grant J.
;
Montgomery, John
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007, 129 (31)
:9568-+

Chaulagain, Mani Raj
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Sormunen, Grant J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Montgomery, John
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[8]
Combined Experimental and Theoretical Study on the Reductive Cleavage of Inert C-O Bonds with Silanes: Ruling out a Classical Ni(0)/Ni(II) Catalytic Couple and Evidence for Ni(I) Intermediates
[J].
Cornella, Josep
;
Gomez-Bengoa, Enrique
;
Martin, Ruben
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2013, 135 (05)
:1997-2009

Cornella, Josep
论文数: 0 引用数: 0
h-index: 0
机构:
Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

Gomez-Bengoa, Enrique
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Basque Country, Dept Organ Chem 1, UPV EHU, San Sebastian 20080, Spain Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

Martin, Ruben
论文数: 0 引用数: 0
h-index: 0
机构:
Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[9]
Ligand-Controlled Regiodivergent Nickel-Catalyzed Annulation of Pyridones
[J].
Donets, Pavel A.
;
Cramer, Nicolai
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2015, 54 (02)
:633-637

Donets, Pavel A.
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland

Cramer, Nicolai
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland
[10]
Mechanistically Inspired Catalysts for Enantioselective Desymmetrizations by Olefin Metathesis
[J].
Fournier, Pierre-Andre
;
Savoie, Jolaine
;
Stenne, Brice
;
Bedard, Marion
;
Grandbois, Alain
;
Collins, Shawn K.
.
CHEMISTRY-A EUROPEAN JOURNAL,
2008, 14 (28)
:8690-8695

Fournier, Pierre-Andre
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

Savoie, Jolaine
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

Stenne, Brice
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

Bedard, Marion
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

Grandbois, Alain
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

Collins, Shawn K.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada