118353-46-1Relevant academic research and scientific papers
Isothiourea-Catalysed Sequential Kinetic Resolution of Acyclic (±)-1,2-Diols
Greenhalgh, Mark D.,Harrer, Siegfried,Neyyappadath, Rifahath M.,Smith, Andrew D.
, p. 1555 - 1560 (2019)
The isothiourea-catalysed acylative kinetic resolution of a range of acyclic (±)-1,2-diols using 1 molpercent of catalyst under operationally simple conditions is reported. Significantly, the bifunctional nature of (±)-1,2-diols was exploited in a sequential double kinetic resolution, in which both kinetic resolutions operate synergistically to provide access to highly enantioenriched products. The principles that underpin this process are discussed, and selectivity factors for the individual kinetic resolution steps are reported in a model system.
Highly Enantioselective Ring-Opening of meso-Epoxides with O- and N-Nucleophiles Catalyzed by a Chiral Sc(III)/bipyridine Complex
Malatinec, ?tefan,Bedná?ová, Eva,Tanaka, Hiroki,Kotora, Martin
supporting information, p. 1249 - 1257 (2021/02/03)
The ring-opening of epoxides is a synthetically significant process widely applied in all kinds of chemistry. Herein, we report the catalytic and highly enantioselective variant of this reaction exploiting our recent endeavors to design and synthesize chi
Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts
Fujii, Kazuki,Mitsudo, Koichi,Mandai, Hiroki,Suga, Seiji
, p. 2778 - 2788 (2017/08/23)
An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).
Scandium-bipyridine-catalyzed, enantioselective alcoholysis of meso-epoxides
Tschoep, Andreas,Marx, Andreas,Sreekanth, Anakallil R.,Schneider, Christoph
, p. 2318 - 2327 (2008/02/08)
The scandium-bipyridine-catalyzed ring-opening of meso-epoxides with aliphatic alcohols has been studied. Aromatic epoxides were ring-opened with >90 % ee furnishing valuable 1,2-diol monoethers in typically good yields whereas aliphatic epoxides gave ris
Scandium-bipyridine-catalyzed enantioselective addition of alcohols and amines to meso-epoxides
Schneider, Christoph,Sreekanth, Anakallil R.,Mai, Enzo
, p. 5691 - 5694 (2007/10/03)
A winning combination of metal and ligand: The catalyst formed in situ from Sc(OTf)3 and bipyridine 1 (10 mol%) mediates the alcoholysis and aminolysis of Mieso-epoxides in high enantioselectivities and furnishes valuable chiral 1,2-diol monoethers 2 and 1,2-amino alcohols 3 as products (PMB = para-methoxybenzyl).
Modular chiral polyether podands and their lanthanide complexes
Aspinall, Helen C.,Greeves, Nicholas,McIver, Edward G.
, p. 10453 - 10463 (2007/10/03)
A novel series of modular chiral polyether podands derived from enantiomerically pure hydrobenzoin and binaphthol has been prepared using a NaH/15-crown-5 mediated Williamson ether synthesis. These new homochiral ligands form catalytically active complexes with lanthanide triflates, two of which have been characterised by X-ray diffraction.
Enantioselective reactions of α-methoxybenzyllithium generated by t-BuLi/chiral bis(oxazoline) complex with aldehydes
Tomooka, Katsuhiko,Wang, Lan-Fang,Komine, Nobuyuki,Nakai, Takeshi
, p. 6813 - 6816 (2007/10/03)
The title reaction is shown to afford the corresponding 1,2-diol monomethyl ethers in moderate-to-high levels of % ee (up to 98%) and % de (up to 90% anti), depending markedly on the aldehyde reactivity. The origin of the enantioselectivity is discussed i
