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- Title
Investigation of a new chiral auxiliary derived chemoenzymatically from toluene: experimental and computational study.
- Authors
Šnajdr, Ivan; Froese, Jordan; Dudding, Travis; Horáková, Pavlína; Hudlický, Tomáš
- Abstract
A tricyclic chiral auxiliary, prepared from the enzymatically derived cis-arene dihydrodiol metabolite of toluene, was investigated as a means of asymmetric induction in several different reactions. The auxiliary was converted to an oxaziridine, and its utility in hydroxylation, providing low levels of enantiomeric excess, was compared with that of Davis's oxaziridine. Insight into the origin of stereoinduction in this reaction is provided and is based on computational Monte Carlo Multiple Minimum (MCMM) searches using the OPLS3 force field. The use of the auxiliary group in the alkylation of appended esters proved disappointing. Diels-Alder cycloaddition of an acrylate, derived from the auxiliary group, with cyclohexadiene furnished a mixture of diastereomeric adducts in essentially equal amounts. The adducts were separated and the corresponding enantiomeric residues were isolated with good enantiomeric excess. Evidence of reasonable levels of asymmetric induction in the above processes was lacking. Experimental and spectral data are provided for all key compounds.
- Subjects
TOLUENE; HYDROXYLATION; OXAZIRIDINE; HETEROCYCLIC compounds; INDUCTION heating
- Publication
Canadian Journal of Chemistry, 2016, Vol 94, Issue 10, p848
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/cjc-2016-0327