87258-61-5Relevant academic research and scientific papers
Compartmentalization and Photoregulating Pathways for Incompatible Tandem Catalysis
Qu, Peiyuan,Kuepfert, Michael,Hashmi, Maryam,Weck, Marcus
, p. 4705 - 4713 (2021)
This contribution describes an advanced compartmentalized micellar nanoreactor that possesses a reversible photoresponsive feature and its application toward photoregulating reaction pathways for incompatible tandem catalysis under aqueous conditions. The
Catalytic Asymmetric Transfer Hydrogenation of trans-Chalcone Derivatives Using BINOL-derived Boro-phosphates
Na, Fei,Lopez, Susana S.,Beauseigneur, Alice,Hernandez, Lucas W.,Sun, Zhuoxin,Antilla, Jon C.
, p. 5953 - 5957 (2020/08/12)
Chiral phosphoric-acid-catalyzed asymmetric reductions of trans-chalcones have been investigated in this work. A BINOL-derived boro-phosphate-catalyzed asymmetric transfer hydrogenation of the carbon-carbon double bond of trans-chalcone derivatives employing borane as a hydride source was realized. This methodology provides a convenient procedure to access chiral dihydrochalone derivatives in high yields and with high enantioselectivities under mild conditions.
Lewis Base-Catalyzed Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Ketones with Trichlorosilane: E/ Z-Isomerization, Regioselectivity, and Synthetic Applications
Sugiura, Masaharu,Ashikari, Yasuhiko,Takahashi, Yuka,Yamaguchi, Koki,Kotani, Shunsuke,Nakajima, Makoto
, p. 11458 - 11473 (2019/10/11)
The chiral bisphosphine dioxide-catalyzed asymmetric conjugate reduction of acyclic β,β-disubstituted α,β-unsaturated ketones with trichlorosilane affords saturated ketones having a stereogenic carbon center at the carbonyl β-position with high enantioselectivities. Because the E/Z-isomerizations of enone substrates occur concomitantly, reduction products with the same absolute configurations are obtained from either (E)- or (Z)-enones. Conjugate reduction is accelerated in the presence of an electron-rich aryl group at the β-position of the enone owing to its carbocation-stabilizing ability. Computational studies were also conducted in order to elucidate the origin of the observed enantioselectivity. The regio- and enantioselective reductions of dienones were realized and applied to the syntheses of ar-turmerone, turmeronol A, mutisianthol, and jungianol, which are optically active sesquiterpenes.
Electronic and Steric Tuning of an Atropisomeric Disulfoxide Ligand Motif and Its Use in the Rh(I)-Catalyzed Addition Reactions of Boronic Acids to a Wide Range of Acceptors
Zhao, Guang-Zhen,Foster, Daven,Sipos, Gellért,Gao, Pengchao,Skelton, Brian W.,Sobolev, Alexandre N.,Dorta, Reto
, p. 9741 - 9755 (2018/09/06)
A novel chiral disulfoxide ligand pair bearing fluorine atoms at the 6 and 6′ position of its atropisomeric backbone, (M,S,S)- and (P,S,S)-p-Tol-6F-BIPHESO, was synthesized. Complexation to a rhodium(I) precursor gave rise to μ-Cl- and μ-OH-bridged rhodiu
Highly efficient synthesis of chiral aromatic ketones: Via Rh-catalyzed asymmetric hydrogenation of β,β-disubstituted enones
Zhang, Tao,Jiang, Jun,Yao, Lin,Geng, Huiling,Zhang, Xumu
, p. 9258 - 9261 (2017/08/22)
A succinct and efficient protocol was developed for the synthesis of chiral aromatic ketones via asymmetric hydrogenation of β,β-disubstituted enones with rhodium catalysts based on chiral bisphosphine thiourea ligands. A series of substrates (17 examples) was smoothly catalyzed to afford the corresponding chiral aromatic ketones in high conversions (>99%) with excellent enantioselectivities (up to 96% ee).
Catalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon-nitrogen and carbon-carbon bonds
Yang, Cui-Feng,Wang, Jian-Yong,Tian, Shi-Kai
supporting information; experimental part, p. 8343 - 8345 (2011/09/16)
An efficient decarboxylative alkylation reaction of β-keto acids with N-benzylic or N-allylic sulfonamides has been developed, for the first time, through sequential cleavage of carbon-nitrogen and carbon-carbon bonds in the presence of 10 mol% of FeCl3.
Base Catalysed Rearrangements involving Ylide Intermediates. Part 15. The Machanism of the Stevens Rearrangement
Ollis, W. David,Rey, Max,Sutherland, Ian O.
, p. 1009 - 1027 (2007/10/02)
The Stevens rearrangement of acyl-stabilised ammonium ylides has been investigated with regard to stereoselectivity, intramolecularity and the formation of products in addition to the rearrangement product.A detailed study of the effects of reaction conditions upon the rearrangement of the ylide derived from the salt (13) has shown that the stereoselectivity (retention of the configuration of the chiral migrating group) and intramolecularity decrease as solvent viscosity decreases.The rearrangement of the salt (13) in water at 0 deg C is essentially intramolecular with virtually complete retention of the configuration of the migrating group.These results, together with the isolation of products that can be rationalised on the basis of random free-radical coupling, indicate that the rearrangement of acyl-stabilised ammonium ylides normally involves a radical pair mechanism.
