24056-33-5Relevant academic research and scientific papers
Cytochrome P450 catalyzed oxidative hydroxylation of achiral organic compounds with simultaneous creation of two chirality centers in a single C-H activation step
Roiban, Gheorghe-Doru,Agudo, Ruben,Reetz, Manfred T.
supporting information, p. 8659 - 8663 (2014/08/18)
Regio- and stereoselective oxidative hydroxylation of achiral or chiral organic compounds mediated by synthetic reagents, catalysts, or enzymes generally leads to the formation of one new chiral center that appears in the respective enantiomeric or diastereomeric alcohols. By contrast, when subjecting appropriate achiral compounds to this type of C-H activation, the simultaneous creation of two chiral centers with a defined relative and absolute configuration may result, provided that control of the regio-, diastereo-, and enantioselectivity is ensured. The present study demonstrates that such control is possible by using wild type or mutant forms of the monooxygenase cytochrome P450 BM3 as catalysts in the oxidative hydroxylation of methylcyclohexane and seven other monosubstituted cyclohexane derivatives.
Nitrilases catalyze key step to conformationally constrained GABA analogous γ-amino acids in high optical purity
Winkler, Margit,Knall, Astrid C.,Kulterer, Martin R.,Klempier, Norbert
, p. 7423 - 7426 (2008/02/12)
(Chemical Equation Presented) Five- and six-membered carbocyclic γ-amino acids were prepared in high enantiomeric purity by nitrilase-mediated transformation of hitherto unreported γ-amino nitriles. The nitrilases investigated reveal a strong enantioprefe
ENZYMATIC IN VITRO REDUCTION OF KETONES. PART 11. THE UNEXPECTED STERIC COURSE OF THE HLAD CATALYZED REDUCTION OF 3-CYANOCYCLOHEXANONE.
Willaert, Jan J.,Lemiere, Guy L.,Dommisse, Roger A.,Lepoivre, Joseph A.,Alderweireldt, Frank C.
, p. 139 - 150 (2007/10/02)
3-Cyanocyclohexanone is a suitable substrate for preparative HLAD reduction, delivering enantiomerically pure (1S,3S)-trans and (1R,3S)-cis alcohols.Details are given on the kinetics of the reduction and the absolute configuration of the products.In contr
Use of Shift Reagent with MTPA Derivatives in 19F NMR Spectroscopy IV - Determination of Enantiomeric Composition for a Variety of Secondary Cycloalkanols. A Survey
Merckx, E. M.,Lepoivre, J. A.,Lemiere, G. L.,Alderweireldt, F. C.
, p. 380 - 387 (2007/10/02)
Chiral secondary cycloalkanols (monpocyclic alcohols) are derivatized to the corresponding (R)-α-methoxy-α-trifluoromethyl-α-phenylacetic acid esters and analysed by 19F NMR in the presence of tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium(III) .Using this method the enantiomeric composition can be measured for severak cyclopentanols, cyclohexanols and cycloheptanols, with a variety of substitution patterns.It is shown that a mixture of four stereoisomeric cycloalkanols, such as cis and trans disubstituted alcohols, can be analysed simultaneously.
