Parallel kinetic resolution of D-labelled 2-aryl-propionic and butanoic acids using quasi-enantiomeric combinations of oxazolidin-2-ones.

The parallel kinetic resolution of racemic 2-aryl-2-deuterio-propionic and butanoic acids using an equimolar combination of quasi-enantiomeric oxazolidin-2-ones is discussed. The levels of diastereoselectivity were high leading to enantiomerically pure D-labeled products in good yield.

Investigations into the use of a polyfluorooctanol as an auxiliary component for an aldol reaction.

Results are reported on the efficiency of polyfluorooctanol as a perfluorous auxiliary component in the aldol reaction between the enolate derived from polyfluorooctyl acetate and 2-fluorobenzaldehyde. Reduction of the corresponding polyfluoro beta-hydroxy ester with Super Hydride gave the required 1,3-diol in good yield.

Mutual kinetic separation of isotopomers of pentafluorophenyl 2-phenyl propionate using quasi-enantiomeric oxazolidinones.

Mutual separation of an equimolar mixture of quasi-enantiomeric [D,13C]-labeled isotopomers of pentafluorophenyl 2-phenylpropionate can be achieved efficiently by use of two quasi-enantiomeric Evans' oxazolidinones. The levels of stereocontrol were high, leading to products with predictable configurations.

Parallel kinetic resolution of an oxazolidinone using a quasi-enantiomeric combination of [D,13C]-isotopomers of pentafluorophenyl 2-phenyl propionate.

Parallel kinetic resolution of Evans' phenylglycine derived oxazolidinone using an equimolar combination of quasi-enantiomeric active esters (derived from [D,13C]-labeled 2-phenylpropionic acid) was achieved. The levels of stereocontrol were high, leading to products with predictable configurations.

Synthesis of enantiomerically pure isotopomers of 2-phenylpropionic acids.

A series of enantiomerically pure [D,(13)C]-labeled isotopomeric 2-phenylpropionic acids were efficiently synthesized using a diastereoselective alkylation and kinetic resolution strategy.

The synthesis and structure of substituted dimenthyl malonate derivatives.

A series of substituted dimenthyl malonate derivatives were efficiently synthesized from dimenthyl malonate using a deprotonation and alkylation strategy. The elucidation of the structure of these derivatives were determined by a combination of X-ray crystallography, NMR and IR spectroscopy.

(-)-Dimenthyl malonate.

The title compound, bis(2-isopropyl-5-methylcyclohex-1-yl) malonate, C(23)H(40)O(4), crystallizes in the monoclinic space group P2(1). In the crystal, the molecule is not C(2) symmetric.

Catalytic Allylic Oxidation of Alkenes Using an Asymmetric Kharasch-Sosnovsky Reaction.

Kharasch and Sosnovsky reported the allylic oxidation of alkenes to give racemic allylic benzoates. This could be achieved efficiently using a tert-butyl perester as the oxidant, in the presence of a copper or cobalt salt. The use of C(2)-symmetric bis(oxazoline) ligands in the presence of copper(I) triflate with cyclic olefinic substrates gave the first synthetically useful asymmetric variant.