Chemoenzymatic Dynamic Kinetic Resolution of β-Halo Alcohols. An Efficient Route to Chiral Epoxides
- 20 November 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (25) , 9006-9010
- https://doi.org/10.1021/jo026157m
Abstract
Enzymatic resolution of β-chloro alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution (conversion up to 99% and ee up to 97%). The efficiency of the DKR is dramatically reduced when β-bromo alcohols are used. The presence of the bromo substituent causes decomposition of the ruthenium catalysts, which triggers the progressive deactivation of the enzyme. The synthetic utility of this procedure has been illustrated by the practical synthesis of different chiral epoxides.Keywords
This publication has 27 references indexed in Scilit:
- Enzymatic Kinetic Resolution and Chemoenzymatic Dynamic Kinetic Resolution of δ-Hydroxy Esters. An Efficient Route to Chiral δ-LactonesThe Journal of Organic Chemistry, 2002
- Dynamic Kinetic Resolution of β-Azido Alcohols. An Efficient Route to Chiral Aziridines and β-Amino AlcoholsThe Journal of Organic Chemistry, 2001
- Enzymatic Resolution of Alcohols Coupled with Ruthenium‐Catalyzed Racemization of the Substrate AlcoholAngewandte Chemie International Edition in English, 1997
- Catalytic Asymmetric DihydroxylationChemical Reviews, 1994
- The chiral pool as a source of enantioselective catalysts and auxiliariesChemical Reviews, 1992
- Pseudomonas lipases as catalysts in organic synthesis: specificity of lipoprotein lipaseJournal of the Chemical Society, Chemical Communications, 1992
- Regioalternating selectivity in the metal salt catalyzed aminolysis of styrene oxideThe Journal of Organic Chemistry, 1991
- Diastereofacial selectivity studies on 3-alkenyl-4,5-diphenyl-4,5-dihydroisoxazolesThe Journal of Organic Chemistry, 1990
- Circular dichroism spectroscopy as a probe for the stereochemistry of aziridine cleavage reactions of mitomycin C. Application to adducts of mitomycin with DNA constituentsJournal of the American Chemical Society, 1984
- LeucomitomycinsJournal of the American Chemical Society, 1984