Enzymatic Kinetic Resolution and Chemoenzymatic Dynamic Kinetic Resolution of δ-Hydroxy Esters. An Efficient Route to Chiral δ-Lactones
- 24 January 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (4) , 1261-1265
- https://doi.org/10.1021/jo016096c
Abstract
A successful kinetic resolution of a racemic mixture of δ-hydroxy esters 1 was obtained via lipase-catalyzed transesterification (E value up to 360). The combination of the enzymatic kinetic resolution with a ruthenium-catalyzed alcohol racemization led to an efficient dynamic kinetic resolution (ee up to 99% and conversion up to 92%). The synthetic utility of this procedure was illustrated by the practical syntheses of δ-lactones (R)-6-methyl- and (R)-6-ethyl-tetrahydropyran-2-one and (S)-5-(tert-butyldimethylsiloxy)heptanal. The former are important building blocks in the synthesis of natural products and biologically active compounds, and the latter is a key intermediate in the synthesis of widely used commercial insecticide Spinosyn A.Keywords
This publication has 17 references indexed in Scilit:
- Enzymatic Reduction of Hydrophobic β,δ-Diketo EstersSynthesis, 2001
- Dynamic Kinetic Resolution of β-Azido Alcohols. An Efficient Route to Chiral Aziridines and β-Amino AlcoholsThe Journal of Organic Chemistry, 2001
- Dynamic kinetic resolution of tert-butyl 4-methyl-3,5-dioxohexanoate through enzymatic reductionChemical Communications, 2000
- Dynamic Kinetic Resolution of Secondary Diols via Coupled Ruthenium and Enzyme CatalysisThe Journal of Organic Chemistry, 1999
- Total Synthesis of Spinosyn A. 2. Degradation Studies Involving the Pure Factor and Its Complete ReconstitutionJournal of the American Chemical Society, 1998
- Synthesis and biological activity of artificial analogs of mycalamide ABioorganic & Medicinal Chemistry Letters, 1997
- Biocatalyst-Mediated Efficient Preparation of Highly Enantiomerically Enriched (R)-5-HexanolideSynlett, 1997
- Enzymatic Resolution of Alcohols Coupled with Ruthenium‐Catalyzed Racemization of the Substrate AlcoholAngewandte Chemie International Edition in English, 1997
- Catalytic disproportionation of aldehydes with ruthenium complexesOrganometallics, 1991
- Asymmetric reduction of the prochiral carbonyl group of aliphatic .gamma.- and .delta.-keto acids by use of fermenting bakers' yeastThe Journal of Organic Chemistry, 1987