94089-47-1Relevant academic research and scientific papers
Rearrangements of α-Diazo-β-hydroxyketones for the Synthesis of Bicyclo[m.n.1]alkanones
Li, Zhengning,Lam, Shuk Mei,Ip, Ignatius,Wong, Wing-Tak,Chiu, Pauline
supporting information, p. 4464 - 4467 (2017/09/11)
Rhodium-catalyzed decomposition of fused bicyclic α-diazo-β-hydroxyketones results in good yields of bridged bicyclo[m.n.1]ketones via a rearrangement pathway.
Silver-Catalyzed 7-exo-dig Cyclization of Silylenolether-ynesulfonamides
Heinrich, Clément F.,Fabre, Indira,Miesch, Laurence
supporting information, p. 5170 - 5174 (2016/04/26)
Cyclization of silylenolether-ynesulfonamides proceeds at ambient temperature under mild reaction conditions under silver catalysis. Bridged compounds were obtained exclusively through 7-exo-dig reactions. The protocol is applicable to a wide range of substrates, thus leading to azabicyclic frameworks. Dig this! Cyclization of silylenolether-ynesulfonamides proceeds at ambient temperature under mild reaction conditions under silver catalysis. Bridged compounds were obtained exclusively through 7-exo-dig reactions. The protocol is applicable to a wide range of substrates, thus leading to azabicyclic frameworks.
Construction of Stereogenic α,α-Disubstituted Cycloalkanones via 1° Amine Thiourea Dual Catalysis: Experimental Scope and Computational Analyses
Kang, Jun Yong,Johnston, Ryne C.,Snyder, Kevin M.,Cheong, Paul Ha-Yeon,Carter, Rich G.
, p. 3629 - 3637 (2016/05/24)
The mechanistic exploration and an expanded experimental discussion of the organocatalyzed, asymmetric Pfau-dAngelo reaction by exploiting a bifunctional 1° amine thiourea catalyst system is disclosed. Notable breadth in substrate scope has been demonstrated on both the cyclic ketone moiety and the α,β-unsaturated electrophile. Exploration into the matched and mismatched selectivity of this process with a ketone containing pre-existing stereocenters has been demonstrated. Computational analyses of the reaction mechanism are reported. In concert with kinetic isotope effect (KIE) experiments, these computational results provide a detailed understanding of the likely mechanism, including the aspects of the organocatalyst scaffold that are critical for stereoselectivity.
Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through the Primary Amine-Catalyzed Michael Addition Reaction of α-Substituted Cyclic Ketones at High Pressure
Horinouchi, Ryo,Kamei, Kouhei,Watanabe, Riki,Hieda, Nobushige,Tatsumi, Naoki,Nakano, Keiji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
, p. 4457 - 4463 (2015/07/27)
The enantioselective Michael addition reaction of α-substituted cyclic ketones with acrylates was efficiently promoted by a primary amine chiral catalyst under high-pressure conditions (1.0 GPa) in tetrahydrofuran. This method was highly successful for the construction of an all-carbon-substituted quaternary-carbon stereogenic center at the α-position of cyclic ketones in high enantiomeric excess, and could be conveniently applied to the formal synthesis of (+)-aspidospermidine. The Michael addition reaction of α-substituted cyclic ketones was efficiently promoted by a primary amine-based organocatalyst under high-pressure conditions (1.0 GPa) in tetrahydrofuran.
Palladium-Catalyzed Decarbonylative Dehydration for the Synthesis of α-Vinyl Carbonyl Compounds and Total Synthesis of (-)-Aspewentins A, B, and C
Liu, Yiyang,Virgil, Scott C.,Grubbs, Robert H.,Stoltz, Brian M.
supporting information, p. 11800 - 11803 (2015/10/05)
The direct α-vinylation of carbonyl compounds to form a quaternary stereocenter is a challenging transformation. It was discovered that δ-oxocarboxylic acids can serve as masked vinyl compounds and be unveiled by palladium-catalyzed decarbonylative dehydr
Intramolecular reductive ketone-alkynoate coupling reaction promoted by (η2-propene)titanium
Schaefer, Christian,Miesch, Michel,Miesch, Laurence
, p. 3253 - 3257 (2012/06/01)
Intramolecular reductive coupling of cycloalkanones tethered to alkynoates in the presence of (η2-propene)titanium was successfully performed to provide hydroxy-esters in a diastereoselective manner. Subsequent lactonization afforded angularly
Primary amine, thiourea-based dual catalysis motif for synthesis of stereogenic, all-carbon quaternary center-containing cycloalkanones
Kang, Jun Yong,Carter, Rich G.
supporting information; experimental part, p. 3178 - 3181 (2012/08/07)
The enantioselective synthesis of α,α-disubstituted cycloalkanones has been developed using a primary amine, thiourea-based dual catalysis pathway. A range of electrophiles and ring sizes are tolerated under the reaction conditions. A possible catalytic c
Room-temperature, acid-catalyzed [2+2] cycloadditions: Suppression of side reactions by using a flow microreactor system
Kurahashi, Kei,Takemoto, Yoshiji,Takasu, Kiyosei
experimental part, p. 270 - 273 (2012/05/05)
Added value: The [2+2] cycloaddition of silyl enol ethers with α,β-unsaturated esters, catalyzed by the superstrong acid triflic imide (Tf2NH), at room temperature in a flow microreactor system is reported. The micororeactor method achieves the [2+2] cycloaddition of unstable silyl enol ethers and acrylates, which is unsuccessful in batch reactors, even at room temperature. Copyright
Regioselective photochemical rearrangement of N-mesyloxylactams
Pichette, Simon,Aubert-Nicol, Samuel,Lessard, Jean,Spino, Claude
, p. 1328 - 1335 (2012/04/05)
N-Mesyloxylactams can undergo ring contraction either by C-3 (usually observed) or C-5 migration. C-5 migration can occur when the C-3 migration product possesses ring strain, but it does not usually compete with C-3 migration. The greater preference for C-3 migration is due to the carbonyl oxygen atom, which greatly stabilizes the intermediate. Studies of the photochemical rearrangement of N-mesyloxylactams showed that the lone pair of the carbonyl oxygen atom, and not the degree of the substitution atthe migrating carbon atoms, is the governing factor in the regioselectivity of the reaction. Copyright
Formal (3+3) cycloaddition of silyl enol ethers catalyzed by trifric imide: Domino michael addition-claisen condensation accompanied with isomerization of silyl enol ethers
Azuma, Takumi,Takemoto, Yoshiji,Takasu, Kiyosei
scheme or table, p. 1190 - 1193 (2011/10/09)
We describe here a Tf2NH-catalyzed formal (3+3) cycloaddition of silyl enol ethers with acrylates as a new domino reaction. In the domino sequence, the catalyst activates Michael addition, deprotonation of the resulting silyloxonium cation and
