112898-44-9Relevant articles and documents
A short asymmetric synthesis of 4,4-disubstituted-γ-butyrolactones from racemic 2-methylcyclohexanone in multigram scale
Pinheiro, Sergio,De Farias, Florence M. C.,Saraiva, Analucia S.,Campos, Marcos P. A.
, p. 2031 - 2034 (1998)
A short and efficient asymmetric synthesis of both enantiomers (R)-1a-c and (S)-1a-c has been performed on a large scale and with high stereoselectivities from 2-methylcyclohexanone.
Asymmetric synthesis of polyfunctionalized allenic esters: Toward the synthesis of an iphionane sesquiterpene
Klein, Aurelie,Miesch, Michel
, p. 2613 - 2617 (2006)
Tetrabutylammonium fluoride (TBAF) reacts smoothly with optically active acetylenic ω-keto esters to afford optically active allenic esters (ee >95%) in high yield. After protection of the hydroxyl group, the addition of morpholine followed by an acidic h
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)
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.
REGIOSELECTIVITY OF ENAMINE REACTIONS, PREFERENTIAL 2,2-DISUBSTITUTION OF 2-METHYLCYCLOHEXANONE IMINES
Hickmott, Peter W.,Rae, Bruce
, p. 2577 - 2580 (1985)
Secondary enamines, derived from imines of unsymmetrical α-substituted ketones, react with electrophilic alkenes at the more substituted position to give α,α-disubstituted ketones on hydrolysis.
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.
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
