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Hillman Reaction (hillman + reaction)

Distribution by Scientific Domains
Chemistry100%

Selected Abstracts

Synthesis of cis-Hedione® and Methyl Jasmonate via Cascade Baylis,Hillman Reaction and Claisen Ortho Ester Rearrangement

HELVETICA CHIMICA ACTA, Issue 12 2005
Christian Chapuis
The exocyclically unsaturated conjugated keto esters 10, obtained via a Claisen ortho ester rearrangement of the allylic hydroxy ketones 9, were either directly hydrogenated or partially isomerized into the endocyclically unsaturated tetrasubstituted didehydrojasmonoid intermediates 14, prior to a more selective hydrogenation with Pd/C in cyclohexane to the disubstituted oxocyclopentaneacetates 15 (Scheme,2). The key intermediates 9 were obtained either by a four-step sequence, including acetal protection/deprotection from enone 1, in the specific case of hydroxy ketone 9a (Scheme,1), or more directly and generally by a Baylis,Hillman reaction from cyclopent-2-en-1-one (16) and the appropriate aldehydes 17 (Scheme,2). The judicious choice of these aldehydes opens versatile modifications for the stereoselective introduction of the partially cis - or epimerized trans -C(2) jasmonoid side chain, while the Baylis,Hillman reaction, catalyzed by chiral [1,1,-binaphthalene]-2,2,-diols (BINOLs) 19 (Scheme,3), may be efficiently conducted in a one-pot cascade fashion including the ortho ester Claisen rearrangement. [source]

Enantioselective Aza-Morita,Baylis,Hillman Reaction Using Aliphatic ,-Amidosulfones as Imine Surrogates

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 4 2010
Nacim Abermil
Abstract The bifunctional catalyst 6,-deoxy-6,-acylamino-,-isocupreidine (1) served both as a base to trigger the in situ generation of N -sulfonylimine from readily available ,-amidosulfones and as a chiral nucleophile to initiate the enantioselective aza-Morita,Baylis,Hillman (aza-MBH) reaction. ,-Methylene-,-amino-,-alkyl carbonyl compounds, difficultly accessible previously, can now be synthesized in excellent yields and enantioselectivities. [source]

Cyclic Enones as Substrates in the Morita,Baylis,Hillman Reaction: Surfactant Interactions, Scope and Scalability with an Emphasis on Formaldehyde

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 7-8 2009
Brett
Abstract Traditionally, cyclic enones and formalin are reactants notorious for displaying problematic behaviour (i.e., poor solubility and low yields) under Morita,Baylis,Hillman (MBH) reaction conditions. The body of research presented herein focuses on the use of surfactants in water as a solvent medium that offers a resolution to many of the issues associated with the MBH reaction. Reaction scope, scalability and small angle X-ray scattering have been studied to assist with the understanding of the reaction mechanism and industrial application. A comparison against known literature methods for reaction scale-up is also discussed. [source]

Dendritic Chiral Phosphine Lewis Bases-Catalyzed Asymmetric Aza-Morita,Baylis,Hillman Reaction of N -Sulfonated Imines with Activated Olefins

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 1 2008
Ying-hao Liu
Abstract A series of polyether dendritic chiral phosphine Lewis bases was synthesized, and successfully applied to the asymmetric aza-Morita,Baylis,Hillman reaction of N -sulfonated imines (N -arylmethylidene-4-methylbenzenesulfonamides) with methyl vinyl ketone (MVK), ethyl vinyl ketone (EVK), and acrolein to give the adducts in good to excellent yields along with up to 97,% ee, which are more effective than our previously reported original chiral phosphine Lewis bases. In addition, the dendrimer-supported chiral phosphine Lewis bases can be easily recovered and reused. [source]

ChemInform Abstract: Baylis,Hillman Reaction Promoted by a Recyclable Protic,Ionic,Liquid Solvent,Catalyst System: DABCO,AcOH,H2O.

CHEMINFORM, Issue 8 2010
Ying Song
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Selenonium Ionic Liquid as Efficient Catalyst for the Baylis,Hillman Reaction.

CHEMINFORM, Issue 52 2009
Eder J. Lenardao
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Chiral N-Thiophosphoryl Imine-Induced Diastereoselective Aza-Morita,Baylis,Hillman Reaction.

CHEMINFORM, Issue 12 2009
Aidang Lu
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: New Entry to 9-Acetyl/Formyl-Substituted 2H,8H-Pyrano[2,3-f]chromen-2-ones Through Baylis,Hillman Reaction.

CHEMINFORM, Issue 52 2008
A. Raghotham
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Morita,Baylis,Hillman Reaction in Water/Ionic Liquids under Microwave Irradiation.

CHEMINFORM, Issue 45 2008
Rodrigo O. M. A. de Souza
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: First Evidence of Proline Acting as a Bifunctional Catalyst in the Baylis,Hillman Reaction Between Alkyl Vinyl Ketones and Aryl Aldehydes.

CHEMINFORM, Issue 29 2008
Michelangelo Gruttadauria
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Dendritic Chiral Phosphine Lewis Bases-Catalyzed Asymmetric Aza-Morita,Baylis,Hillman Reaction of N-Sulfonated Imines with Activated Olefins.

CHEMINFORM, Issue 21 2008
Ying-hao Liu
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: An Unexpected Organocatalytic Asymmetric Tandem Michael/Morita,Baylis,Hillman Reaction.

CHEMINFORM, Issue 16 2008
Silvia Cabrera
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Aza-Baylis,Hillman Reaction of Salicyl N-Tosylimines with Methyl Vinyl Ketone, Ethyl Vinyl Ketone or Phenyl Vinyl Ketone.

CHEMINFORM, Issue 5 2008
Ming-Juan Qi
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: The Aza-Morita,Baylis,Hillman Reaction of N-Thiophosphoryl Imines Catalyzed by 1,3,5-Triaza-7-phosphaadamantane (PTA) , Convenient Synthesis of ,-Methylene-,-amino Ketone or Acid Derivatives.

CHEMINFORM, Issue 1 2008
Xinyuan Xu
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

A Novel Ytterbium/Perfluoroalkylated-Pyridine Catalyst for Baylis,Hillman Reaction in a Fluorous Biphasic System.

CHEMINFORM, Issue 47 2007
Wen-Bin Yi
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]

Aminocatalysis of the Baylis,Hillman Reaction: An Important Solvent Effect.

CHEMINFORM, Issue 22 2007
Huw J. Davies
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]

Novel Application of the Baylis,Hillman Reaction.

CHEMINFORM, Issue 16 2007
V. V. Trifonov
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]

One-Pot Synthesis of Substituted Indole N-Oxides: TiCl4 -Mediated Baylis,Hillman Reaction of ,-Oxo Cyclic Ketene-S,S-acetal with o-Nitrobenzaldehydes and Subsequent Intramolecular Cyclization.

CHEMINFORM, Issue 36 2006
Wei Pan
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]

The Baylis,Hillman Reaction with Chiral ,-Amino Aldehydes under Racemization-Free Conditions.

CHEMINFORM, Issue 25 2006
Fernando Coelho
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]

Chiral Binaphthyl-Derived Amine-Thiourea Organocatalyst-Promoted Asymmetric Morita,Baylis,Hillman Reaction.

CHEMINFORM, Issue 4 2006
Jian Wang
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

Dual Catalyst Control in the Enantioselective Intramolecular Morita,Baylis,Hillman Reaction.

CHEMINFORM, Issue 1 2006
Carrie E. Aroyan
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

Diastereoselective Baylis,Hillman Reaction: First Use of Chiral 2,3-Epoxy Aldehydes as Novel Electrophiles.

CHEMINFORM, Issue 4 2005
Palakodety Radha Krishna
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

Polymer-Supported Lewis Bases for the Baylis,Hillman Reaction.

CHEMINFORM, Issue 47 2003
Jin-Wen Huang
No abstract is available for this article. [source]

1-Benzopyran-4(4H)-ones as Novel Activated Alkenes in the Baylis,Hillman Reaction: A Simple and Facile Synthesis of Indolizine-Fused Chromones.

CHEMINFORM, Issue 36 2003
Deevi Basavaiah
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

Baylis,Hillman Reaction of Isatin Derivatives: Isatins as a New Entry for the Baylis,Hillman Reaction.

CHEMINFORM, Issue 15 2003
Yun Mi Chung
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

ChemInform Abstract: Successful Baylis,Hillman Reaction of Acrylamide with Aromatic Aldehydes.

CHEMINFORM, Issue 27 2002
Chengzhi Yu
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Isatin Derivatives Are Reactive Electrophilic Components for the Baylis,Hillman Reaction.

CHEMINFORM, Issue 26 2002
Simon J. Garden
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Carbonyl and Olefin Reactivities for the Baylis,Hillman Reaction of Fluorocarbonyls.

CHEMINFORM, Issue 33 2001
P. Veeraraghavan Ramachandran
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

Asymmetric Aza-Morita,Baylis,Hillman Reactions of Alkyl Vinyl Ketones with N -Protected Imines or In Situ Generated N -Protected Imines

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 21 2010
Xiao-Yang Guan
Abstract DABCO-catalyzed aza-MBH reactions of N -Boc imines with MVK and EVK have been thoroughly investigated in the paper. The asymmetric version of this aza-MBH reaction was also systematically investigated by using a chiral amine or a chiral phosphane catalyst. It was found that most of the N -protected imines are suitable substrates under the mild reaction conditions and are able to give the corresponding adducts in moderate yields with high ee values. The TQO- or LB1-catalyzed aza-MBH reactions of N -protected ,-amidoalkyl phenyl sulfones or ,-amidoalkyl p -tolyl sulfones with MVK could be well conducted, which provides a facile and direct route to obtain highly enantioselective aza-MBH adducts. The Boc protecting group of the aza-MBH product could be easily removed under acidic conditions to give the corresponding ,-methylene-,-amino ketone or ,-methylene-,-amino alcohol derivatives in good yields. [source]

Enantioselective Trifunctional Organocatalysts for Rate- Enhanced Aza-Morita,Baylis,Hillman Reactions at Room Temperature

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 3 2009
Jean-Marc Garnier
Abstract A Brønsted acid-activated trifunctional organocatalyst, based on the BINAP scaffold, was used for the first time to catalyze aza-Morita-Baylis,Hillman reactions between N -tosylimines and methyl vinyl ketone with fast reaction rates and good enantioselectivity at room temperature. This trifunctional catalyst, containing a Lewis base, a Brønsted base, and a Brønsted acid, required acid activation to confer its enantioselectivity and rate improvement for both electron-rich and electron-deficient imine substrates. The role of the amino Lewis base of 1a was investigated and found to be the activity switch in response to an acid additive. The counterion of the acid additive was found to influence not only the excess ratio but also the sense of asymmetric induction. [source]