351464-36-3Relevant academic research and scientific papers
Enantioselective, Stereoconvergent Resolution Copolymerization of Racemic cis-Internal Epoxides and Anhydrides
He, Guang-Hui,Ren, Bai-Hao,Chen, Shi-Yu,Liu, Ye,Lu, Xiao-Bing
, p. 5994 - 6002 (2021/02/11)
Unprecedented enantioselective resolution copolymerization of racemic cis-internal epoxides and anhydrides was mediated by dinuclear aluminum complexes with multiple chirality, affording optically active polyesters with two contiguous stereogenic centers, and the unreacted substrates in good enantioselectivity. Unexpected stereoconvergence is observed in this resolution copolymerization, where the selectivity factor for the enantioselective formation of copolymer significantly exceeds the kinetic resolution coefficient based on the unreacted epoxide at various conversions. Catalytic activity and copolymer enantioselectivity are strongly influenced by the phenolate ortho-substituents of the ligand set, as well as the axial linker and its chirality. An enantiopure binaphthol-linked bimetallic AlIII complex allows stereoconvergent access to the stereoregular semi-crystalline polyesters and a concomitant kinetic resolution of the epoxide substrates.
Arene cis-Diol Dehydrogenase-Catalysed Regio- and Stereoselective Oxidation of Arene-, Cycloalkane- and Cycloalkene-cis-diols to Yield Catechols and Chiral α-Ketols
Boyd, Derek R.,Sharma, Narain D.,Berberian, M. Victoria,Cleij, Marcel,Hardacre, Christopher,Ljubez, Vera,McConville, Gareth,Stevenson, Paul J.,Kulakov, Leonid A.,Allen, Christopher C. R.
supporting information, p. 1881 - 1894 (2015/06/02)
Benzene cis-diol dehydrogenase and naphthalene cis-diol dehydrogenase enzymes, expressed in Pseudomonas putida wild-type and Escherichia coli recombinant strains, were used to investigate regioselectivity and stereoselectivity during dehydrogenations of arene, cyclic alkane and cyclic alkene vicinal cis-diols. The dehydrogenase-catalysed production of enantiopure cis-diols, α-ketols and catechols, using benzene cis-diol dehydrogenase and naphthalene cis-diol dehydrogenase, involved both kinetic resolution and asymmetric synthesis methods. The chemoenzymatic production and applications of catechol bioproducts in synthesis were investigated.
Stereocontrolled synthesis of contiguous C(sp3) - C(aryl) bonds by lanthanide(III)-catalyzed domino aryl-claisen [3,3]-sigmatropic rearrangements
Ramadhar, Timothy R.,Kawakami, Jun-Ichi,Lough, Alan J.,Batey, Robert A.
supporting information; experimental part, p. 4446 - 4449 (2010/12/24)
A domino [3,3]-sigmatropic aryl-Claisen rearrangement of cyclic and acyclic bisaryloxy-substituted alkenes can be performed in high yield by using Ln(fod)3 catalysis to obtain bisphenolic products incorporating two contiguous aryl - C(sp3) bonds. Stereospecific rearrangement was observed for cyclic substrates. The precursor diaryl ethers were typically synthesized from the corresponding diols by double arylation procedures using either copper catalyzed coupling of aryltrifluoroborate salts or by S NAr reaction.
New C2-symmetrical 1,2-diphosphanes for the efficient rhodium-catalyzed asymmetric hydroboration of styrene derivatives
Demay, Steandphane,Volant, Florence,Knochel, Paul
, p. 1235 - 1238 (2007/10/03)
A double [2,3] sigmatropic rearrangement enables the fast synthesis of novel C2-symmetrical 1,2-diphosphanes in good yields. These phosphanes (for example, 1; c-Hex = cyclohexyl) are highly efficient ligands for the rhodium-catalyzed asymmetric hydroboration of a wide variety of styrenes (see scheme). cod = 1,5-cyclooctadiene; DME = 1,2-dimethoxyethane.
Enantioselective preparation of a novel chiral 1,2-diamine
Demay, Stéphane,Kotschy, Andras,Knochel, Paul
, p. 863 - 866 (2007/10/03)
A short enantioselective preparation of (1S,2S)-trans-1,2-diamino-3-cyclohexene using a double [3,3]-sigmatropic rearrangement of an allylic bis(imidate) is described (Overman rearrangement). The starting chiral diol is conveniently obtained by enzymatic resolution.
Enantioselective Ester Hydrolyses Employing Rhizopus nigricans. A Method of Preparing and Assigning the Absolute Stereochemistry of Cyclic Alcohols
Kasai, Masaji,Kawai, Ken-ichi,Imuta, Mitsuru,Ziffer, Herman
, p. 675 - 679 (2007/10/02)
The mold Rhizopus nigricans has been used to hydrolyze enantioselectively the acetates of several series of benzocycloalken-3-ols and 2-substituted cycloalkanols to yield chiral alcohols.The configurations of the alcohols formed were established.The absolute stereochemistries of 25 of the 26 alcohols obtained were found to conform to a generalization based on the effective sizes of substituents on the carbinol carbon.The relative sizes of substituents required for agreement were identical with those employed in Horeu's method of establishing the absolute stereochemistry of the same compounds.The use of these microbially mediated hydrolyses to assign the absolute stereochemistry of cyclic secondary alcohols is compared to Horeau's method and to the use of empirical relations between the absolute stereochemistry of an enantiomer and the order, relative to its antipode, in which it is eluted from a chiral (Pirkle) column.
