6249-81-6Relevant academic research and scientific papers
Selective Aerobic Oxygenation of Tertiary Allylic Alcohols with Molecular Oxygen
Zhu, Bencong,Shen, Tao,Huang, Xiaoqiang,Zhu, Yuchao,Song, Song,Jiao, Ning
supporting information, p. 11028 - 11032 (2019/07/08)
Aerobic epoxidation of tertiary allylic alcohols remains a significant challenge. Reported here is an efficient and highly chemoselective copper-catalyzed epoxidation and semipinacol rearrangement reaction of tertiary allylic alcohols with molecular oxygen. The solvent 1,4-dioxane activates dioxygen, thereby precluding the addition of a sacrificial reductant.
Enantioselective Bromolactonization of Trisubstituted Olefinic Acids Catalyzed by Chiral Pyridyl Phosphoramides
Nishikawa, Yasuhiro,Hamamoto, Yuhta,Satoh, Rika,Akada, Naho,Kajita, Shuhei,Nomoto, Marina,Miyata, Megumi,Nakamura, Madoka,Matsubara, Chinatsu,Hara, Osamu
supporting information, p. 18880 - 18885 (2018/12/04)
Enantioselective bromolactonization of trisubstituted olefinic acids producing synthetically useful chiral lactones with two contiguous asymmetric centers has remained mainly unexplored except for the 6-exo cyclization mode. In this work, the 5-exo- and 6
Nonenzymatic kinetic resolution of α-aryl substituted allylic alcohols catalyzed by acyl transfer catalyst Np-PIQ
Jiang, Shan-Shan,Gu, Bo-Qi,Zhu, Ming-Yu,Yu, Xingxin,Deng, Wei-Ping
, p. 1187 - 1191 (2015/02/19)
Chiral α-aryl substituted allylic alcohols are important versatile synthetic intermediates. We report here an effective nonenzymatic kinetic resolution of racemic α-aryl substituted allylic alcohols by introducing different aryl groups with acyl transfer
Non-enzymatic acylative kinetic resolution of primary allylic amines
Kolleth, Amandine,Cattoen, Martin,Arseniyadis, Stellios,Cossy, Janine
supporting information, p. 9338 - 9340 (2013/10/01)
A non-enzymatic acetyl transfer-based kinetic resolution of primary allylic amines is reported. The process involves the use of (1S,2S)-1 in conjunction with a supported ammonium salt and affords the corresponding enantio-enriched N-acetylated allylic ami
N-BuLi/LiCH2CN-mediated one-carbon homologation of aryl epoxides into conjugated allyl alcohols
Tomioka, Takashi,Sankranti, Rambabu,Yamada, Tsuyoshi,Clark, Courtney
supporting information, p. 5099 - 5101 (2013/10/22)
A series of styrene oxides in the presence of a 1:1 mixture of n-butyllithium (n-BuLi) and lithioacetonitrile (LiCH2CN) in THF are converted into one-carbon homologated allyl alcohols in an unusual regioselective manner.
C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization
Chen, Feng,Tan, Chong Kiat,Yeung, Ying-Yeung
supporting information, p. 1232 - 1235 (2013/03/28)
A catalytic asymmetric bromocyclization of trisubstituted olefinic amides that uses a C2-symmetric mannitol-derived cyclic selenium catalyst and a stoichiometric amount of N-bromophthalimide is reported. The resulting enantioenriched pyrrolidine products, which contain two stereogenic centers, can undergo rearrangement to yield 2,3-disubstituted piperidines with excellent diastereoselectivity and enantiospecificity.
Arylation of allyl alcohols in organic and aqueous media catalyzed by oxime-derived palladacycles: Synthesis of β-arylated carbonyl compounds
Alacid, Emilio,Najera, Carmen
, p. 2572 - 2584 (2008/09/19)
A 4-hydroxyacetophenone oxime-derived palladacycle catalyzes the Mizoroki-Heck reaction of allyl alcohols with aryl iodides, bromides, and chlorides in aqueous and organic solvents. The reaction takes place in the presence of dicyclohexylmethylamine or cesium carbonate as bases, the addition of tetrabutylammonium bromide (TBAB) as additive for aryl bromides and chlorides being necessary. Under these reaction conditions, β-arylated aldehydes and ketones are mainly obtained using a rather low loading of palladium (0.1-1 mol%). Similar catalytic activity is shown by a Kaiser oxime resin-derived palladacycle, which allows one to perform recycling and reusing experiments with low Pd leaching. The high regio- and chemoselectivity observed supported that these palladacycles, working as a source of Pd(0) species, operates mainly through a neutral mechanism. This methodology has been applied to the synthesis of important β-arylated carbonyl compounds, such as 4-phenylbutan-2-one, 4-(4-hydroxyphenyl)butan-2-one, dihydrochalcones, the anti-inflamatory nabumetone, and the fragance β-lilial. γ-Arylation is observed in the reactions of allyl alcohol and but-3-en-2-ol with 2-iodoaniline giving mainly the corresponding quinolines. The same tendency is observed in the case of 1,1-dimethylallyl alcohol affording either γ-arylated alcohols or (E)-1-arylisoprenes.
Chemoenzymatic dynamic kinetic resolution of allylic alcohols: A highly enantioselective route to acyloin acetates
Bogar, Krisztian,Vidal, Pilar Hoyos,Alcantara Leon, Andres R.,Baeckvall, Jan-E.
, p. 3401 - 3404 (2008/02/12)
Dynamic kinetic resolution (DKR) of a series of sterically hindered allylic alcohols has been conducted with Candida antarctica lipase B (CALB) and ruthenium catalyst 1. The optically pure allylic acetates obtained were subjected to oxidative cleavage to
Studies on the Cu(I)-catalyzed regioselective anti-carbometallation of secondary terminal propargylic alcohols
Lu, Zhan,Ma, Shengming
, p. 2655 - 2660 (2007/10/03)
A highly regioselective Cu(I)-catalyzed anti-carbometallation of secondary terminal propargylic alcohols with 1° alkyl or aryl Grignard reagents affording 2-substituted allylic alcohols was developed. By using this method, optically active allylic alcohols can be prepared from the optically active propargylic alcohols without obvious loss of the enantiopurity. The cyclic organometallic intermediate formed may undergo an iodination or a Pd(0)-catalyzed coupling reaction to afford stereo-defined allylic alcohols.
AMINE-BASED AND AMIDE-BASED INHIBITORS OF SEMICARBAZIDE-SENSITIVE AMINE OXIDASE (SSAO) ENZYME ACTIVITY AND VAP-1 MEDIATED ADHESION USEFUL FOR TREATMENT OF DISEASES
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Page/Page column 86, (2010/02/13)
Compositions and methods are disclosed for inhibiting semicarbazide-sensitive amine oxidase (SSAO), also known as vascular adhesion protein-1 (VAP-1). The compounds disclosed are amine-containing and amide-containing compounds. The compounds and compositions are useful for treatment of diseases, including inflammation, inflammatory diseases and autoimmune disorders.
