A range of 2-substituted-2,4-dimethyl-8-oxabicyclo[3.2.1]octan-3-ones 13-18 are available in four steps and in states of high optical purity. The fluoroketone 18 was shown to be a catalyst for the asymmetric epoxidation of stilbene, (E )-methylstilbene, phenylstilbene and chalcone (59-68% ee at 24-67% conversion) using Oxone ® as the primary oxidant.

The sulfoxide thermolysis of the diastereoisomeric methyl (3R,4aS,10aR)-6-methoxy-1-methyl-3-(phenylsulfinyl)-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-3-carboxylates 3a and 3'b in toluene yields, by loss of benzenesulfenic acid, an almost 1 : 1 mixture of the vinylogous urethane 2b and the isomeric a-aminomethyl enoate 2a. When this elimination is performed in acetic acid, the enoate 2a is formed rather selectively. The same solvent effects on the regioselectivity of the elimination of benzenesulfenic acid are observed with a simple sulfoxide of ethyl piperidine-3-carboxylate (7).Introduction. ± In the course of new product developments, we were interested in the conversion of methyl (3R,4aR,10aR)-6-methoxy-1-methyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-3-carboxylate (1) [1] to the corresponding unsaturated methyl (4aS,10aR)-6-methoxy-1-methyl-1,2,4a,5,10,10a-hexahydrobenzo[g]quinoline-3-carboxylate (2a) [2] (Scheme 1).

Oxirane derivativesOxirane derivatives R 0030 2-Substituted-2,4-endo-dimethyl-8-oxabicyclo[3.2.1]octan-3-ones as Catalysts for the Asymmetric Epoxidation of Some Alkenes withOxone®. -The synthesis of the used ketone is described. The absolute configuration of this ketone and another similar compound is determined by X-ray analysis. -(KLEIN*, S.; ROBERTS, S. M.;