18180-77-3Relevant academic research and scientific papers
Enantioselective nucleophilic opening of meso epoxides by organolithium reagents
Alexakis, Alexandre,Vrancken, Emmanuel,Mangeney, Pierre
, p. 1165 - 1167 (1998)
Aryl lithium reagents, complexed with (-)-sparteine, react enantioselectively with cyclic meso epoxides, to afford chiral aryl cyclanols. The enantiomeric excess, though moderate (27-87%), is the best in the literature for such a reaction. Activation by B
Palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones for the synthesis oftranscycloalkanols through dynamic kinetic resolution under acidic conditions
Li, Xiang,Zhao, Zi-Biao,Chen, Mu-Wang,Wu, Bo,Wang, Han,Yu, Chang-Bin,Zhou, Yong-Gui
supporting information, p. 5815 - 5818 (2020/06/03)
The first efficient palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones has been described through dynamic kinetic resolution under acidic conditions, providing a facile access to chiraltranscycloalkanol derivatives with excellent enantioselectivities.
Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Br?nsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions
Gheewala, Chirag D.,Hirschi, Jennifer S.,Lee, Wai-Hang,Paley, Daniel W.,Vetticatt, Mathew J.,Lambert, Tristan H.
supporting information, p. 3523 - 3527 (2018/03/21)
An enantioselective catalytic inverse-electron-demand Diels-Alder reaction of salicylaldehyde acetal-derived oxocarbenium ions and vinyl ethers to generate 2,4-dioxychromanes is described. Chiral pentacarboxycyclopentadiene (PCCP) acids are found to be effective for a variety of substrates. Computational and X-ray crystallographic analyses support the unique hypothesis that an anion with point-chirality-induced helical chirality dictates the absolute sense of stereochemistry in this reaction.
Copper(II)-catalyzed meta-selective direct arylation of α-aryl carbonyl compounds
Duong, Hung A.,Gilligan, Ruth E.,Cooke, Michael L.,Phipps, Robert J.,Gaunt, Matthew J.
supporting information; experimental part, p. 463 - 466 (2011/03/16)
Strong competition: A method for the meta-selective arylation of the highly versatile α-aryl carbonyl motif using diaryliodonium salts is described. In this CuII-catalyzed process the remote carbonyl group is capable of overpowering even strongly para-directing functionalities to form the elusive meta-products (see scheme). Remarkably, the arylation process can also operate under metal-free conditions.
Organolithium/chiral Lewis base/BF3: A versatile combination for the enantioselective desymmetrization of meso-epoxides
Vrancken, Emmanuel,Alexakis, Alexandre,Mangeney, Pierre
, p. 1354 - 1366 (2007/10/03)
BF3 can be used in combination with organolithium/strong Lewis base complexes for the enantioselective nucleophilic ring-opening or the carbenoidic rearrangement of various meso-oxiranes with excellent yields and ee values of up to 87%. Mechanistic aspects of these reactions are considered. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Tin(IV) chloride-chiral pyrogallol derivatives as new Lewis acid-assisted chiral Bronsted acids for enantioselective polyene cyclization
Kumazawa, Keiko,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 2551 - 2554 (2007/10/03)
(Matrix Presented) New Lewis acid-assisted Bronsted acids (LBAs), tin(IV) chloride-2,6-dialkoxyphenols, serve as artificial cyclases for biomimetic polyene cyclization. For example, the enantioselective cyclization of 4-(homogeranyl)toluene using tin(IV) chloride-2,6-di[(1′R,2′R)- trans-2′-(3″,5″-xylyl)cyclohexanoxy]-phenol gave a trans-fused tricyclic compound with 85% ee.
Enzymatic resolution of trans-2-arylcyclohexan-1-ols using crude chicken liver esterase (CCLE) as biocatalyst
Basavaiah,Rao
, p. 223 - 234 (2007/10/02)
Homochiral trans-2-arylcyclohexan-1-ols were synthesized via crude chicken liver esterase (CCLE) mediated enantioselective hydrolysis of the corresponding racemic acetates.
