13677-45-7Relevant academic research and scientific papers
Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol
Biswal, Priyabrata,Samser, Shaikh,Meher, Sushanta Kumar,Chandrasekhar, Vadapalli,Venkatasubbaiah, Krishnan
, p. 413 - 419 (2021/11/01)
One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.
Potassium Base-Promoted Diastereoselective Synthesis of 1,3-Diols from Allylic Alcohols and Aldehydes through a Tandem Allylic-Isomerization/Aldol–Tishchenko Reaction
Sai, Masahiro
, p. 4053 - 4056 (2021/10/25)
This study reports the first base-promoted aldol–Tishchenko reactions of allylic alcohols with aldehydes initiated by allylic isomerization. The reaction enables the diastereoselective synthesis of a variety of 1,3-diols with three contiguous stereogenic centers. Unlike commonly reported systems, our method allows the use of readily available allylic alcohols as nucleophiles instead of enolizable aldehydes and ketones.
Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols
Chan, Chieh-Kai,Tsai, Yu-Lin,Chang, Meng-Yang
, p. 3368 - 3376 (2017/05/22)
Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.
Triazolium salts as appropriate catalytic scaffolds for 1,4-additions to α,β-unsaturated carbonyls
Bratko, Ielyzaveta,Guisado-Barrios, Gregorio,Favier, Isabelle,Mallet-Ladeira, Sonia,Teuma, Emmanuelle,Peris, Eduardo,Gomez, Montserrat
, p. 2160 - 2167 (2014/04/17)
1,2,3-Triazole derivatives containing a rigid dihydroanthracenyl skeleton are suitable precursors for both organometallic and organo-based catalysts. A Rh-carbene complex and the triazolium salt efficiently catalyzed the 1,4-additions of C- and heterodonor reagents to α,β-unsaturated carbonyl substrates, respectively. Copyright
Lithium amidoborane, a highly chemoselective reagent for the reduction of α,β-unsaturated ketones to allylic alcohols
Xu, Weiliang,Zhou, Yonggui,Wang, Ruimin,Wu, Guotao,Chen, Ping
experimental part, p. 367 - 371 (2012/01/13)
Lithium amidoborane (LiNH2BH3, LiAB for short), is capable of chemoselectively reducing α,β-unsaturated ketones to the corresponding allylic alcohols at ambient temperature. A mechanistic study shows that the reduction is via a double hydrogen transfer process. The protic H(N) and hydridic H(B) in amidoborane add to the O and C sites of the carbonyl group, respectively.
Effect of charge distribution on selective hydrogenation of conjugated enones catalyzed by iridium complexes
Spogliarich,Farnetti,Graziani
, p. 1965 - 1976 (2007/10/02)
Chemoselectivity in the reduction of substituted conjugated enones catalyzed by iridium/phosphine systems appears to be slightly dependent on the charge distribution around the carbonyl group of the substrates: electron, withdrawing groups enhance the reduction rate of the ketonic function. Enantioselectivity, in the case of the catalytic system studied, appears to be related essentially to the steric hindrance in the substrate.
