39599-18-3Relevant academic research and scientific papers
Applications of Baylis-Hillman Coupling Products: a Remarkable Reversal of Stereochemistry from Esters to Nitriles: a Simple Synthesis of (2E)-2-Methylalk-2-en-1-ols and (2Z)-2-Methylalk-2-enenitriles
Basavaiah, Deevi,Sarma, Pakala K. S.
, p. 955 - 957 (2007/10/02)
Reaction of methyl 3-acetoxy-2-methylenealkanoates with the reducing agent, lithium aluminium hydride (LAH): ethanol (1:1), provides (2E)-2-methylalk-2-en-1-ols, whereas, reaction of 3-acetoxy-2-methylenealkanenitriles with the same reagent provides (2Z)-2-methylalk-2-enenitriles in high yields.
SYNTHESIS OF (Z)-PREDOMINANT α,β-UNSATURATED NITRILES FROM ENONE CYANOHYDRIN DIETHYL PHOSPHATES: APPLICATION TO THE SYNTHESIS OF (+/-)-NUCIFERAL, (+/-)-(E)-AND -(Z)-NUCIFEROL, AND (+/-)-MANICONE
Yoneda, Ryuji,Harusawa, Shinya,Kurihara, Takushi
, p. 3163 - 3168 (2007/10/02)
Enone cyanohydrin diethyl phosphates reaced regio- and stereo-selectively with a variety of organocopper reagents to give γ-coupling products, (Z)-predominant alk-2-enenitriles.The methodology was applied to the synthesis of (+/-)-nuciferal, (+/-)-(E)- an
A NEW AND FACILE SYNTHESIS OF 2-ALKENENITRILES USING 3-BUTEN-2-ONE CYANOHYDRIN DIETHYL PHOSPHATE; APPLICATION TO (+/-)-(E)-NUCIFEROL SYNTHESIS
Yoneda, Ryuji,Harusawa, Shinya,Kurihara, Takushi
, p. 913 - 915 (2007/10/02)
3-Buten-2-one cyanohydrin diethyl phosphate reacted regio- and stereo-selectively with a variety of dialkyl cuprates and ethoxycarbonylmethylcopper giving γ-coupling products, 2-alkene nitriles, one of which was used to synthesize (+/-)-(E)-Nuciferol.Keyw
FACILE SYNTHESIS OF (E)-ALLYLIC ALCOHOLS BY ACID-CATALYZED MODIFICATION OF THE MISLOW-EVANS REARRANGEMENT OF ALLYLIC SULFOXIDES
Masaki, Yukio,Sakuma, Kazuhiko,Kaji, Kenji
, p. 2531 - 2534 (2007/10/02)
The Mislow-Evans rearrangement of α,β- and α,γ-disubstituted allylic sulfoxides (2) to (E)-allylic alcohols (4) was found to occur under acidic conditions.By combination of this method with a catalytic oxidation of allylic sulfides (1), a novel one-pot tr
Facile Regio- and Stereo-specific Allylic Oxidation of gem-Dimethyl Olefins via Addition of Benzenesulphenyl Chloride. Synthesis of Allylic Oxygenated Terpenes
Masaki, Yukio,Hashimoto, Kinji,Sakuma, Kazuhiko,Kaji,Kenji
, p. 1289 - 1295 (2007/10/02)
Novel and facile terminal trans-allylic and internal allylic oxidations of the gem-dimethyl olefin terminus of the terpenoids (1) are described which take place site-, regio-, and stereo-specificially via the same intermediate adduct between benzenesulphenyl chloride and (1).By this method, the allylic oxygenated terpenes (+/-)-nuciferal (11), (+/-)-ar-turmerone (12), (+/-)-ipsdienol (3c), neotorreyol (2e), (+/-)-6-hydroxydendrolasin (3e), and 6-oxodendrolasin (14) were synthesized.
Aldolisation dirigee avec l'acroleine. Methode de synthese stereoselective de doubles liaisons trisubstituees fonctionnalisees. Application a la synthese du (+/-)-Z-chloronuciferal et du (+/-)-E-nuciferol
Depezay, Jean-Claude,Merrer Le, Yves
, p. 306 - 312 (2007/10/02)
To direct the aldolisation reaction in such a way that an aldehyde reacts upon the electrophilic carbonyl group of a ketone or of another aldehyde, it is necessary to mask the aldehyde and to transform it into a nucleophile.The present article presents an approach to this problem concerning unsaturated aldehydes and describes the condensation between the α-carbanion of acrolein and several carbonyl compounds. Aldol condensation at -70 degC, between 1,1-diethoxy-2-lithio-2-propene and several aldehydes leads to β-hydroxy-α-methylene acetals.These secondary allylic alcohols are stereoselectively transformed into trisubstituted functionalised olefinic compounds (Z-α-chlormethyl-α,β-unsaturated aldehydes and E-α-methyl-α,β-unsaturated primary alcohols). This method is illustrated by the syntheses of (+/-)-Z-chloronuciferal and (+/-)-E-nuciferol.
