Online citations, reference lists, and bibliographies.
← Back to Search

Regio- And Stereoselective Synthesis Of 2-amino-1,3-diene Derivatives By Ruthenium-catalyzed Coupling Of Ynamides And Ethylene.

Nozomi Saito, K. Saito, M. Shiro, Yoshihiro Sato
Published 2011 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy Visualize in Litmaps
Share
Reduce the time it takes to create your bibliography by a factor of 10 by using the world’s favourite reference manager
Time to take this seriously.
Get Citationsy
A ruthenium-catalyzed hydrovinylation-type cross-coupling of ynamides and ethylene proceeds via ruthenacyclopentene to give 2-aminobuta-1,3-diene derivatives in a highly regioselective manner. It was also demonstrated that 2-aminobuta-1,3-diene derivatives reacted with various dienophiles or singlet oxygen to give a cyclic enamide derivative.
This paper references
10.1016/0040-4039(76)80116-5
Syntheses of furanoterpenes: perillaketone, α-clausenane, (±)-ipomeamarone, and (±)-epiipomeamarone
K. Kondo (1976)
10.1055/S-1981-29592
PREPARATION AND DIELS-ALDER REACTIONS OF HETERO-SUBSTITUTED 1,3-DIENES
M. Petrzilka (1981)
10.1016/S0040-4020(01)86780-6
Camphor derivatives as chiral auxiliaries in asymmetric synthesis
W. Oppolzer (1987)
10.1055/S-1987-27972
The ground state and excited state reactions of enamides
A. L. Campbell (1987)
10.1351/pac199062071241
Camphor as a natural source of chirality in asymmetric synthesis
W. Oppolzer (1990)
10.1016/S0065-3055(08)60498-0
Chemistry of the Cyciopentadienyl Bisphosphine Ruthenium Auxiliary
S. Davies (1990)
10.1126/SCIENCE.1962206
The atom economy--a search for synthetic efficiency.
B. Trost (1991)
10.1071/CH9920109
Stereocontrolled Functionalization of Cycloheptadiene by Nucleophile Addition to Cycloheptadienyliron Complexes - Preparation and Reactions of 6-Methylcyclohepta-2,4-dienol Derivatives
A. Pearson (1992)
10.1002/ANIE.199502591
Atom Economy—A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way
B. Trost (1995)
10.1016/S0040-4039(98)01580-9
Ruthenium-catalyzed coupling of unactivated olefins with unactivated alkynes
M. Murakami (1998)
10.1021/OM990129L
Hydrovinylation and [2+2] Cycloaddition Reactions of Alkynes and Alkenes Catalyzed by a Well-Defined Cationic Ruthenium−Alkylidene Complex
C. Yi (1999)
10.1016/S0040-4020(01)00681-0
Recent advances in the chemistry of ynamines and ynamides
C. A. Zificsak (2001)
10.1021/OL017298Y
Synthesis of cyclic dienamide using ruthenium-catalyzed ring-closing metathesis of ene-ynamide.
N. Saito (2002)
10.1016/S1381-1169(01)00500-3
Ruthenium-catalyzed addition of olefinic C–H bonds in conjugate enones to acetylenes to give conjugate dienones
F. Kakiuchi (2002)
10.1021/OL020097P
The first successful base-promoted isomerization of propargyl amides to chiral ynamides. Applications in ring-closing metathesis of ene-ynamides and tandem RCM of diene-ynamides.
J. Huang (2002)
10.1021/JA029747A
Novel alkenylative cyclization using a ruthenium catalyst.
M. Mori (2003)
10.1021/OL027209X
Concise and stereoselective synthesis of enamides and dienamides by a titanium-mediated coupling method.
R. Tanaka (2003)
10.1016/J.TET.2005.11.080
Practical preparation of N-(1-alkynyl)sulfonamides and their synthetic utility in titanium alkoxide-mediated coupling reactions
S. Hirano (2006)
10.1016/J.TET.2005.11.083
Synthesis of cyclic dienamide using ruthenium-catalyzed ring-closing metathesis of ene–ynamide
M. Mori (2006)
10.1016/J.TET.2005.11.086
Preparation of trifluoromethylated ynamines and their reactions with some electrophilic reagents
T. Ishihara (2006)
10.1021/OM058053I
Unpredicted Cyclization of an Enyne Having a Keto-Carbonyl Group on an Alkyne Using a Ruthenium Catalyst under Ethylene Gas
D. Tanaka (2006)
10.1002/ANIE.200701356
Regio- and stereoselective synthesis of enamides and dienamides by ruthenium-catalyzed co-oligomerization of N-vinylamides with alkenes or alkynes.
H. Tsujita (2007)
10.1002/ADSC.200700371
Ruthenium/Halide Catalytic System for CC Bond Forming Reaction between Alkynes and Unsaturated Carbonyl Compounds
T. Nishimura (2007)
10.1021/JA071954T
Ruthenium-catalyzed [2 + 2 + 2] cocyclization of diene-yne.
D. Tanaka (2007)
10.1021/ol800995r
Rhodium-catalyzed regio- and stereoselective codimerization of alkenes and electron-deficient internal alkynes leading to 1,3-dienes.
Yu Shibata (2008)
10.1021/OM8008266
Ruthenium-Catalyzed Alkenylative Cyclization via Insertion of Alkene into Ruthenacyclopentene
M. Mori (2008)
10.1002/anie.200705558
Palladium-catalyzed intermolecular ene-yne coupling: development of an atom-efficient Mizoroki-Heck-type reaction.
A. T. Lindhardt (2008)
10.1021/ol801534e
Nickel-catalyzed highly regioselective multicomponent coupling of ynamides, aldehydes, and silane: a new access to functionalized enamides.
N. Saito (2008)
10.1021/OM801181A
Ruthenium-Catalyzed Cyclodimerization of Allenynes
N. Saito (2009)
10.1021/ol901616b
Ruthenium-catalyzed [2 + 2] cycloaddition of allenynes leading to a bicyclo[4.2.0]octa-1(8),5-diene skeleton.
N. Saito (2009)
10.1021/ja900946h
Stereoselective synthesis of multisubstituted enamides via rhodium-catalyzed carbozincation of ynamides.
B. Gourdet (2009)
10.1002/anie.200901928
The ruthenium-catalyzed hydrovinylation of internal alkynes by acrylates: an atom economic approach to highly substituted 1,3-dienes.
N. M. Neisius (2009)
10.1021/ol8028324
A regioselective Ru-catalyzed alkene-alkyne coupling to form (Z,Z)-1,3-dienes.
B. Trost (2009)
10.1021/jo901658v
Preparation of multisubstituted enamides via rhodium-catalyzed carbozincation and hydrozincation of ynamides.
B. Gourdet (2009)
10.1021/ol900647s
Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure.
R. Hayashi (2009)
10.1021/ol902821w
Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition.
R. Hayashi (2010)
10.1021/ol1004615
Cu-catalyzed oxidative amidation of propiolic acids under air via decarboxylative coupling.
W. Jia (2010)
10.1021/ja105435y
Stereoselective synthesis of β-hydroxy enamines, aminocyclopropanes, and 1,3-amino alcohols via asymmetric catalysis.
P. Valenta (2010)
10.1002/anie.200905817
Ynamides: versatile tools in organic synthesis.
G. Evano (2010)
10.1021/jo101238x
Nucleophilic cycloaromatization of ynamide-terminated enediynes.
Andrei A. Poloukhtine (2010)
10.1002/MASY.200900035
Ring‐Closing Metathesis of Ene‐Ynamide: Application to the Synthesis of Medium‐Sized Cyclic Dienamide
Hideaki Wakamatsu (2010)
10.1002/anie.201004328
Catalytic asymmetric dihydroxylation of enamides and application to the total synthesis of (+)-tanikolide.
B. Gourdet (2010)
10.1021/ol1008679
Stereoselective additions of thiyl radicals to terminal ynamides.
B. Banerjee (2010)
10.1016/J.TET.2010.06.021
Rhodium-catalyzed carbometalation of ynamides with organoboron reagents
B. Gourdet (2010)
10.1055/S-0030-1258023
Copper-Free Sonogashira Cross-Couplingof Ynamides: Easy Access to ­Various Substituted Ynamidesfrom Nonsubstituted Ynamides
H. Wakamatsu (2010)
10.1021/ol1008685
Access to 2,5-diamidopyrroles and 2,5-diamidofurans by au(i)-catalyzed double hydroamination or hydration of 1,3-diynes.
S. Kramer (2010)
10.1021/ol101322k
Copper-catalyzed alkynylation of amides with potassium alkynyltrifluoroborates: a room-temperature, base-free synthesis of ynamides.
Kévin Jouvin (2010)
10.3987/COM-10-S(E)122
Asymmetric synthesis of γ-siloxyenamides via chiral auxiliary-mediated diastereoselective coupling of ynamides, aldehydes, and silane by nickel catalyst
N. Saito (2010)
10.3987/COM-10-S(E)87
Unprecedented synthesis of N,N-divinylamines by Tf2NH-catalyzed reaction of ynamide with ketimine
Naoya Shindoh (2010)
10.1016/J.TET.2010.05.045
Alkynes to (E)-enolates using tandem catalysis: stereoselective anti-aldol and syn-[3,3]-rearrangement reactions
N. Grimster (2010)
10.1021/cr100003s
Ynamides: a modern functional group for the new millennium.
Kyle A Dekorver (2010)
10.5012/BKCS.2010.31.03.570
Radical Additions of Arenethiols to Ynamides for the Selective Synthesis of N-((Z)-2-(Arylsulfanyl)-1-alkenyl)amides †
A. Sato (2010)
10.1021/ol101418d
Copper-catalyzed Ficini [2 + 2] cycloaddition of ynamides.
H. Li (2010)
10.1021/ol100769p
Rhodium-catalyzed annulation of ynamides with bifunctional arylboron reagents.
B. Gourdet (2010)
10.1002/ADSC.201000792
Highly Regio- and Stereoselective Nickel-Catalyzed Addition of Dialkyl Phosphites to Ynamides: an Efficient Synthesis of β-Aminovinylphosphonates
A. Fadel (2011)
10.1002/anie.201007753
Enantioselective Ficini reaction: ruthenium/PNNP-catalyzed [2+2] cycloaddition of ynamides with cyclic enones.
C. Schotes (2011)
10.1021/ol200270t
Gold-catalyzed synthesis of benzil derivatives and α-keto imides via oxidation of alkynes.
Chengfu Xu (2011)
10.1021/jo2000308
Synthesis of polycyclic benzofused nitrogen heterocycles via a tandem ynamide benzannulation/ring-closing metathesis strategy. Application in a formal total synthesis of (+)-FR900482.
Xiao Yin Mak (2011)
10.1021/ol200269h
Metal-free halonium mediated acetate shifts of ynamides to access α-halo acrylamides/acrylimides.
S. Kramer (2011)
10.1039/c0cc02736g
Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers.
Paul W Davies (2011)



This paper is referenced by
10.1002/adsc.202001342
A Catalytic Construction of Indoles via Formation of Ruthenium Vinylidene Species from N ‐Arylynamides
Masanori Tayu (2021)
10.1039/c9nj04880d
An insight into regioselectivity in the transformation through a ruthenacycle
Sayori Kiyota (2020)
10.1039/d0cs00769b
Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications.
Ciarán C Lynch (2020)
10.1039/c9qo00747d
Applications of sulfuryl fluoride (SO2F2) in chemical transformations
Ravindar Lekkala (2019)
10.1002/EJOC.201900604
Direct Hydroheteroarylation of Ynamides with 2H‐Tetrazoles: Regio‐ and Stereoselective Synthesis of (Z)‐α‐Tetrazole Enamides
Jiekun Zhu (2019)
10.1039/C8QO01388H
SO2F2 mediated dehydrative cross-coupling of alcohols with electron-deficient olefins in DMSO using a Pd-catalyst: one-pot transformation of alcohols into 1,3-dienes
R. Lekkala (2019)
10.1002/chem.201905175
Synthesis of (Z)-β-(carbonylamino)alkenylindium via Regioselective Anti-carboindation of Ynamides and Its Transformation to Multisubstituted Enamides.
Kyoungmin Kang (2019)
10.1021/acs.orglett.9b01766
Additive- and Ligand-Free Cross-Coupling Reactions between Alkenes and Alkynes by Iridium Catalysis.
Yaling Sun (2019)
10.1016/J.TETLET.2018.11.016
Ruthenium dihydride complexes as enyne metathesis catalysts
Martin A. Dolan (2018)
10.1021/acs.orglett.7b00695
Amide Directed Cross-Coupling between Alkenes and Alkynes: A Regio- and Stereoselective Approach to Substituted (2Z,4Z)-Dienamides.
Keke Meng (2017)
10.1039/c7cc03229c
A biosynthetically inspired route to substituted furans using the Appel reaction: total synthesis of the furan fatty acid F5.
R. Lee (2017)
10.1002/anie.201709128
Ynamide Preactivation Allows a Regio- and Stereoselective Synthesis of α,β-Disubstituted Enamides.
L. L. Baldassari (2017)
10.1039/c7cc07777g
Ruthenium-catalyzed olefinic C-H alkenylation of enol-carbamates: highly stereo-selective synthesis of (Z,Z) and (Z,E)-butadienes.
Tingyan Li (2017)
10.1002/ANGE.201709128
Regio‐ und stereoselektive Synthese α,β‐disubstituierter Enamide durch Voraktivierung von Inamiden
L. L. Baldassari (2017)
10.1039/C6OB01234E
Enantioselective synthesis of β-amino acid derivatives via nickel-promoted regioselective carboxylation of ynamides and rhodium-catalyzed asymmetric hydrogenation.
Nozomi Saito (2016)
10.1039/c6ob00454g
Pd(0)-catalyzed cross-coupling of allyl halides with α-diazocarbonyl compounds or N-mesylhydrazones: synthesis of 1,3-diene compounds.
K. Wang (2016)
10.1039/C5RA10569B
Regio- and stereoselective synthesis of ensulfonamides/enamides via catalyst-free intermolecular addition of indoles/pyrroles/imidazole to allenamides
Hong-he Li (2015)
10.1002/asia.201403399
Nickel-promoted highly regioselective carboxylation of aryl ynol ether and its application to the synthesis of chiral β-aryloxypropionic acid derivatives.
N. Saito (2015)
10.1021/ACSCATAL.5B01075
Computational Exploration of Mechanism and Selectivities of (NHC)Nickel(II)hydride-Catalyzed Hydroalkenylations of Styrene with α-Olefins
Xin Hong (2015)
10.1021/acs.orglett.5b01859
Stereoselective Synthesis of (2Z)-2,4-Dienamides via NBS-Mediated Allyloxyl Addition-Claisen Rearrangement-Dehydrobromination Cascade Reaction of Ynsulfonamides.
R. Ding (2015)
10.1002/EJOC.201501060
Base-Promoted Approach to Highly Functionalized Conjugated Dienes through Enamine Migration
Yulei Zhao (2015)
10.1039/C4GC01328J
Metal-free hydroacyloxylation and hydration reactions of ynamides: synthesis of α-acyloxyenamides and N-acylsulfonamides
Shijie Xu (2015)
10.1021/jo501894j
Preparation of (Z)-α,β-disubstituted enamides via palladium-catalyzed addition of boronic acids to ynamides.
Yuanfa Yang (2014)
10.1007/3418_2014_82
C–C Bond Formation on Activation of Alkynes and Alkenes with (C5R5)Ru Catalysts
S. Dérien (2014)
10.1002/anie.201402098
Exploring bis(cyclometalated) ruthenium(II) complexes as active catalyst precursors: room-temperature alkene-alkyne coupling for 1,3-diene synthesis.
J. Zhang (2014)
10.1039/c3cc49069f
An unprecedented Pd-catalyzed trans-addition of boronic acids to ynamides.
Yuanfa Yang (2014)
10.1021/ol5026926
Ruthenium catalyzed cycloisomerization of silicon-tethered 1,7-enynes to give exocyclic 1,3-dienes.
L. Kaminsky (2014)
10.1002/anie.201303916
Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.
Vaneet Saini (2013)
10.1016/J.COMPTC.2012.12.005
New bimolecular mechanistic pathway for 1,3-hydrogen shift in allenamide and allene system: A theoretical prediction
A. Basak (2013)
10.1016/J.TETLET.2013.09.072
Palladium-catalyzed cross-coupling of cyclopropylmethyl N-tosylhydrazones with aromatic bromides: an easy access to multisubstituted 1,3-butadienes
Q. Yang (2013)
10.1002/ANGE.201303916
Übergangsmetallkatalysierte C‐C‐Kupplungen mit Ethylen im Labormaßstab
Vaneet Saini (2013)
10.1039/C3CY00084B
Metal catalysed hydrovinylation
R.Ma. Ceder (2013)
See more
Semantic Scholar Logo Some data provided by SemanticScholar