Enantioselective Ene Reaction of Cyclopentadiene and α,β‐Enals Catalyzed by a Diphenylprolinol Silyl Ether
Angewandte Chemie International EditionPublished 26 September 2006
Hiroaki Gotoh, Ryouhei Masui, Hiroshi Ogino, Mitsuru Shoji, Yujiro Hayashi
Citations120
SJR quartileQ1
SJR score5.55
SNIP2.47
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
Abstract
The opposite result: A diphenylprolinol silyl ether promotes an intermolecular enantioselective ene reaction of α,β-enals with cyclopentadiene. This is the first example of cyclopentadiene acting as the ene component, and not the diene, with α,β-enals.
Keywords
Chemistry
Angewandte Chemie International EditionIn the Golden Age of Organocatalysis
2,574 Citations2004Peter I. Dalko, Lionel Moisan
The diverse examples show that in recent years organocatalysis has developed within organic chemistry into its own subdiscipline, whose "Golden Age" has already dawned.
Journal of the American Chemical SocietyNew Strategies for Organic Catalysis: The First Highly Enantioselective Organocatalytic Diels−Alder Reaction
1,667 Citations2000Kateri A. Ahrendt, Christopher J. Borths +1 more
Angewandte Chemie International EditionDiphenylprolinol Silyl Ethers as Efficient Organocatalysts for the Asymmetric Michael Reaction of Aldehydes and Nitroalkenes
1,257 Citations2005Yujiro Hayashi, Hiroaki Gotoh +2 more
Angewandte Chemie International EditionEnantioselective Organocatalyzed α Sulfenylation of Aldehydes
956 Citations2005Mauro Marigo, Tobias C. Wabnitz +2 more
NatureControl of four stereocentres in a triple cascade organocatalytic reaction
907 Citations2006Dieter Enders, Matthias R. M. Hüttl +2 more
The development of an asymmetric organocatalytic triple cascade reaction for the synthesis of tetra-substituted cyclohexene carbaldehydes, described as biomimetic, as they are reminiscent of tandem reactions that may occur during biosyntheses of complex natural products.
Angewandte ChemieIm Goldenen Zeitalter der Organokatalyse
726 Citations2004Peter I. Dalko, Lionel Moisan
Journal of the American Chemical SocietyA General Organocatalyst for Direct α-Functionalization of Aldehydes: Stereoselective C−C, C−N, C−F, C−Br, and C−S Bond-Forming Reactions. Scope and Mechanistic Insights
633 Citations2005Johan Franzén, Mauro Marigo +4 more
The development of a general organocatalyst for the alpha-functionalization of aldehydes, via an enamine intermediate, is presented and mechanistic insight into the reaction course applying nonlinear effect studies, kinetic resolution, and computational investigations leading to an understanding of the properties of the alpha,alpha-diarylprolinol silyl ether catalysts.
Chemical ReviewsAsymmetric ene reactions in organic synthesis
608 Citations1992Koichi Mikami, Masaki Shimizu
Angewandte Chemie International Edition in EnglishThe Ene Reaction
526 Citations1969H. M. R. Hoffmann
Angewandte Chemie International EditionEnantioselective Formation of Stereogenic Carbon–Fluorine Centers by a Simple Catalytic Method
465 Citations2005Mauro Marigo, Doris Fielenbach +3 more
Journal of the American Chemical SocietyAsymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes with Hydrogen Peroxide
451 Citations2005Mauro Marigo, Johan Franzén +3 more
Journal of the American Chemical SocietyThe First General Enantioselective Catalytic Diels−Alder Reaction with Simple α,β-Unsaturated Ketones
451 Citations2002Alan B. Northrup, David W. C. MacMillan
The first general approach to enantioselective catalysis of the Diels-Alder reaction with simple ketone dienophiles has been accomplished with the use of iminium catalysis and a new chiral amine catalyst has been developed that allows a variety of monodentate cyclic and acyclic ketones to successfully participate in enantiOSElective [4 + 2] cycloadditions.
Journal of the American Chemical SocietyAsymmetric Multicomponent Domino Reactions and Highly Enantioselective Conjugated Addition of Thiols to α,β-Unsaturated Aldehydes
438 Citations2005Mauro Marigo, Tobias L. Schulte +2 more
An organocatalytic asymmetric multicomponent domino and a conjugated addition reaction to α,β-unsaturated aldehydes are presented, which give enantiopure amino−thiols in moderate to good yields and excellent enantioselectivities.
Angewandte Chemie International Edition in EnglishIntramolecular Ene Reactions in Organic Synthesis
402 Citations1978Wolfgang Oppolzer, Victor Snieckus
Angewandte ChemieEnantioselective Organocatalyzed α Sulfenylation of Aldehydes
371 Citations2005Mauro Marigo, Tobias C. Wabnitz +2 more
Angewandte Chemie International EditionOrganocatalytic Conjugate Addition of Malonates to α,β‐Unsaturated Aldehydes: Asymmetric Formal Synthesis of (−)‐Paroxetine, Chiral Lactams, and Lactones
325 Citations2006Sven Brandau, Aitor Landa +3 more
Journal of the American Chemical SocietyEnantioselective Organocatalytic Intramolecular Diels−Alder Reactions. The Asymmetric Synthesis of Solanapyrone D
250 Citations2005Rebecca M. Wilson, Wendy S. Jen +1 more
The first direct enantioselective organocatalytic intramolecular Diels-Alder reaction has been accomplished and the use of iminium catalysis has provided a new catalytic strategy for the enantiOSElective [4 + 2] cycloisomerization of a wide variety of tethered diene-enal systems.
Organic LettersDiphenylprolinol Methyl Ether: A Highly Enantioselective Catalyst for Michael Addition of Aldehydes to Simple Enones
245 Citations2005Yonggui Chi, Samuel H. Gellman
Diphenylprolinol methyl ether catalyzes intermolecular Michael addition of simple aldehydes to relatively nonactivated enones with the highest enantioselectivities reported to date (95-99% ee) and significantly lower catalyst loadings than have been typical in this arena.
Journal of the American Chemical SocietyDesign of an Organocatalyst for the Enantioselective Diels−Alder Reaction with α-Acyloxyacroleins
219 Citations2005Kazuaki Ishihara, Kazuhiko Nakano
The first enantioselective organocatalytic Diels-Alder reaction between alpha-substituted acroleins, such as alpha-acyloxyacrolein, and not only cyclic but also acyclic dienes is realized.
Journal of the American Chemical SocietyOne-Pot Organocatalytic Domino Michael-Aldol and Intramolecular S<sub>N</sub>2 Reactions. Asymmetric Synthesis of Highly Functionalized Epoxycyclohexanone Derivatives
198 Citations2006Mauro Marigo, Søren Bertelsen +2 more
The development of the organocatalytic asymmetric one-pot Michael-Darzens condensation giving highly functionalized complex epoxycyclohexanone derivatives with up to four chiral centers with high diversity in substitution pattern is presented.
ChemInformEnantioselective Organocatalytic Intramolecular Diels—Alder Reactions. The Asymmetric Synthesis of Solanapyrone D.
185 Citations2005Rebecca M. Wilson, Wendy S. Jen +1 more
Angewandte ChemieEnantioselective Formation of Stereogenic Carbon–Fluorine Centers by a Simple Catalytic Method
184 Citations2005Mauro Marigo, Doris Fielenbach +3 more
Journal of the American Chemical SocietyEnantioselective Organocatalytic Aminomethylation of Aldehydes: A Role for Ionic Interactions and Efficient Access to β<sup>2</sup>-Amino Acids
171 Citations2006Yonggui Chi, Samuel H. Gellman
The beta-amino aldehydes from this process bear a substituent adjacent to the carbonyl and can be efficiently converted to protected beta2-aminos acids, which are important building blocks for beta-peptide foldamers that display useful biological activities.
Tetrahedron LettersDirect organocatalytic asymmetric epoxidation of α,β-unsaturated aldehydes
141 Citations2005Henrik Sundén, Ismail Ibrahem +1 more
Angewandte ChemieIntramolekulare En-Reaktionen in der organischen Synthese
131 Citations1978Wolfgang Oppolzer, Victor Snieckus
Organic LettersChiral 1,1‘-Binaphthyl-2,2‘-diammonium Salt Catalysts for the Enantioselective Diels−Alder Reaction with α-Acyloxyacroleins
120 Citations2006Akira Sakakura, Kenji Suzuki +2 more
A diammonium salt of chiral 1,1'-binaphthyl-2,2'-diamine and trifluoromethanesulfonimide (Tf(2)NH) shows excellent catalytic activity and enantioselectivity for the Diels-Alder reaction of alpha-acyloxyacroleins with cyclic dienes.
Angewandte ChemieOrganocatalytic Conjugate Addition of Malonates to α,β‐Unsaturated Aldehydes: Asymmetric Formal Synthesis of (−)‐Paroxetine, Chiral Lactams, and Lactones
117 Citations2006Sven Brandau, Aitor Landa +3 more
Chemical CommunicationsDirect catalytic asymmetric anti-selective Mannich-type reactions
115 Citations2006Ismail Ibrahem, Armando Córdova
The simple chiral pyrrolidine catalyzed asymmetric anti-selective Mannich-type reaction is presented; the reaction gives the corresponding amino acid derivatives with 10:1- >19:1 dr and 97-99% ee.
Organic & Biomolecular ChemistryOrganocatalytic asymmetric epoxidation reactions in water–alcohol solutions
99 Citations2005Wei Zhuang, Mauro Marigo +1 more
The diastereo- and enantioselective organocatalytic epoxidation of alpha,beta-unsaturated aldehydes in aqueous solutions is presented and a highly stereoselectives reaction has been developed.
Journal of Synthetic Organic Chemistry JapanRecent Progress in the Asymmetric Organocatalysis
79 Citations2005Yujiro Hayashi
Angewandte Chemie International Edition in EnglishCatalytic Asymmetric Carbonyl–Ene Reactions
65 Citations1995David J. Berrisford, Carsten Bolm
Chemistry LettersAsymmetric Intramolecular Ene Reaction Catalyzed by a Chiral Titanium Alkoxide
42 Citations1988Koichi Narasaka, Yujiro Hayashi +1 more
TetrahedronCatalysis with inorganic cations. VI. The effect of chiral bis-oxazoline-magnesium perchlorate catalysts on chemo- and enantioselectivity of intramolecular Hetero Diels-Alder and ene reaction
36 Citations1996Giovanni Desimoni, Giuseppe Faita +2 more
The Journal of Organic ChemistryCycloaddition routes to tricyclo[5.4.01,7.02,9]undecanes: a direct total synthesis of (+)-longifolene via an intramolecular Diels-Alder strategy
35 Citations1993Bo Lei, Alex G. Fallis
The Journal of Organic ChemistryPyrrolidine-catalyzed reactions between .alpha.,.beta.-unsaturated carbonyl compounds and cyclopentadiene: a convenient approach to 1,2- and 1,5-dihydropentalenes
32 Citations1989Axel G. Griesbeck
Israel Journal of ChemistryAsymmetric Intramolecular Ene Reaction Catalyzed by a Chiral Titanium Reagent and Synthesis of (—)‐ε‐Cadinene
29 Citations1991Koichi Narasaka, Yujiro Hayashi +2 more
Angewandte ChemieKatalytische asymmetrische Carbonyl‐En‐Reaktionen
23 Citations1995David J. Berrisford, Carsten Bolm
The Journal of Organic ChemistrySynthesis of brexan-2-one and ring-expanded congeners
21 Citations1992Alfred G. Stern, Alex Nickon
Journal of the American Chemical SocietyProton coupling constants in methycyclopentadienes
18 Citations1972V. A. Korenevskii, N. M. Sergeev
Helvetica Chimica ActaZur Lenkung der intramolekularen <i>Diels</i>‐<i>Alder</i>‐Reaktion von Cyclopentadienen mit olefinischen Substituenten
14 Citations1983Olof Wallquist, Max Rey +1 more