220365-75-3Relevant academic research and scientific papers
A short efficient preparation of (+) and (-)-trans-2-phenylcyclohexanol
Carpenter, Bryon E.,Hunt, Ian R.,Keay, Brian A.
, p. 3107 - 3108 (1996)
Both enantiomers of trans-2-phenylcyclohexanol (1) (Whitesell's auxiliary) have been prepared in a facile three step sequence starting from phenylmagnesium bromide and cyclohexene oxide using Lipase PS30 to facilitate the resolution of the racemic alcohol
Diastereoselective and enantioselective alkaline-hydrolysis of 2-aryl-1-cyclohexyl acetate: a CAL-B catalyzed deacylation/acylation tandem process
Belkacemi, Fatma Zahra,Merabet-Khelassi, Mounia,Aribi-Zouioueche, Louisa,Riant, Olivier
supporting information, p. 1644 - 1650 (2017/10/12)
Candida antarctica lipase proved to be a particularly efficient lipase for the resolution of racemic 2-arylcyclohexyl acetate in hydrolysis reaction with Na2CO3 in an organic medium. The (1R,2S)-trans-2-arylcyclohexanols 2a–2d were obtained with high ee values (up to >99%) and the selectivity reached E > 200. The influence of the enol ester and the solvent on (±)-trans-2-arylcyclohexanol in the CAL-B catalyzed acylation was also studied and compared with the deacylation. The CAL-B exhibits a better affinity for the alkaline hydrolysis reaction compared with acylation with the enol esters in the same organic solvents. The best conditions were applied to resolve a stereoisomeric mixture cis/trans-2-phenyl-1-cyclohexanol and its corresponding acetate by acylation and deacylation. The obtained results show a highly enantio- and diastereoselectivity of the CAL-B during the acylation and the deacylation in favor of the trans-(R)-enantiomer product. The resolution of a mixture of cis/trans-2-arylcyclohexanols was an easy, convenient approach to provide only one stereoisomer of a mixture of four with high enantiomeric excess.
Kinetic resolution of secondary alcohols by chiral dmap derivatives prepared by the Ugi multicomponent reaction
Mandai, Hiroki,Irie, Shunsuke,Akehi, Masaru,Yuri, Kazunobu,Yoden, Masaaki,Mitsudo, Koichi,Suga, Seiji
, p. 329 - 340 (2013/03/28)
The kinetic resolution of secondary alcohols was examined by new chiral DMAP derivatives, which can readily be prepared by the Ugi multicomponent reaction in a one-pot operation. The initial screening of DMAP derivatives indicated that the catalyst bearing L-valine with an S configuration at the a-position of amide showed the best stereoselectivity factor. After the reaction conditions were optimized with (S,S)-4a in the kinetic resolution of secondary alcohols, various acyclic and cyclic secondary alcohols could be resolved with an s -factor of up to 12.
(S)-proline-derived catalysts for the acylative kinetic resolution of alcohols: A remote structural change allows a complete selectivity switch
Gleeson, Oliver,Gun'Ko, Yurii K.,Connon, Stephen J.
supporting information, p. 1728 - 1734 (2013/09/02)
A systematic preliminary study has identified a suite of catalysts, all readily prepared and derived from (S)-proline, which differ by a remote substituent only. If this substituent is capable of hydrogen-bond donation the catalyst will promote the resolu
Homobenzotetramisole: An effective catalyst for kinetic resolution of aryl-cycloalkanols
Birman, Vladimir B.,Li, Ximin
supporting information; experimental part, p. 1115 - 1118 (2009/04/07)
Homobenzotetramisole (HBTM), a ring-expanded analogue of the previously reported catalyst BTM, displays higher catalytic activity and a different structure-selectivity profile. It displays good enantioselectivities in kinetic resolution of secondary benzylic alcohols but is particularly effective for 2-aryl-substituted cycloalkanols.
Lipase AK-mediated synthesis of both antipodes of 2-phenyl- and 2-(1-naphthyl)cyclohexanols in enantiomerically pure form
She, Yi-Hsuan,Wu, Chen-Fan,Shia, Kak-Shan,Wu, Jen-Dar,Peddinti, Rama Krishna,Liu, Hsing-Jang
, p. 749 - 752 (2007/10/03)
Both (R,S)- and (S,R)-enantiomers of 2-phenylcyclohexanol and 2-(1-naphthyl)cyclohexanol were prepared in enantiomerically pure form and in excellent chemical yields by lipase AK (Pseudomonas fluorescens)-catalyzed kinetic acetylation of racemic alcohols
A new nucleophilic catalyst for kinetic resolution of racemic sec-alcohols
Jeong, Kyu-Sung,Kim, Soong-Hyun,Park, Hyun-Jin,Chang, Kyoung-Jin,Kwan, Soo Kim
, p. 1114 - 1115 (2007/10/03)
A new tertiary amine-based nucleophilic catalyst, derived from a simple combination of commercially available compounds, affords good to excellent kinetic resolution of racemic sec-alcohols.
Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: An approach to kinetic resolution of secondary alcohols of broad structural scope
Copeland,Miller
, p. 6496 - 6502 (2007/10/03)
An assay employing a fluorescently labeled split and pool peptide library has been applied to the discovery of a new class of octapeptide catalysts for the kinetic resolution of secondary alcohols. A highly diverse library of peptide-based catalysts was synthesized on solid-phase synthesis beads such that each individual bead was co-functionalized with (i) a uniform loading of a pH-sensitive fluorophore and (ii) a unique peptidebased catalyst. The library was then screened for activity in acylation reactions employing (±)-sec-phenylethanol as the substrate and acetic anhydride as the acylation agent. From the most active catalysts, a lead peptide (4) was identified that provides a selectivity-factor (krel) of 8.2 upon resynthesis and evaluation under homogeneous conditions. A "directed" second-generation split and pool peptide library was synthesized such that the new peptide sequences in the library were biased toward the lead structure. Random samples of the second generation library were screened in single bead assays that revealed several new peptide-based catalysts that afford improved selectivities in kinetic resolutions. Peptide catalyst 13 proves effective for the kinetic resolution of sec-phenylethanol (krel = 20), as well as eight other secondary alcohols of a broad substrate scope (krel = 4 to > 50).
Enzymic Preparation of Enantiomerically Pure Cyclohexanols: Ester Synthesis by Irreversible Acyl Transfer
Laumen, Kurt,Seemayer, Robert,Schneider, Manfred P.
, p. 49 - 51 (2007/10/02)
Enantiomerically pure cyclohexanols are prepared enzymically via irreversible acyl transfer; they are valuable substitutes for 8-phenylmenthols and are potentially useful as chiral auxiliaries.
