Topic
Wieland–Miescher ketone
About: Wieland–Miescher ketone is a research topic. Over the lifetime, 88 publications have been published within this topic receiving 938 citations. The topic is also known as: 8a-Methyl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione.
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TL;DR: In this paper, an efficient preparation procedure of optically pure Wieland-Miescher ketone, (8aR)-(−)-3,4,8,8a-tetrahydro-8amethyl-1,6(2H,7H)-naphthalenedione (1), is described, and its absolute stereochemistry is confirmed by the CD exciton chirality method to its derivatives.
Abstract: An efficient preparation procedure of optically pure Wieland-Miescher ketone, (8aR)-(−)-3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione (1), is described, and its absolute stereochemistry is confirmed by the application of the CD exciton chirality method to its derivatives
39 citations
TL;DR: Both enantiomers of Wieland-Miescher ketone, in a highly enantiomerically enriched form, became readily available by a newly developed kinetic resolution with yeast-mediated reduction by an established proline-mediated asymmetric Robinson annulation.
Abstract: Both enantiomers of Wieland-Miescher ketone [3,4,8, 8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione], in a highly enantiomerically enriched form, became readily available by a newly developed kinetic resolution with yeast-mediated reduction. From a screening of yeast strains, Torulaspora delbrueckii IFO 10921 was selected. The collected cells of this strain, obtained by an incubation in a glucose medium, smoothly reduced only the isolated carbonyl group of the (S)-enantiomer, while the (R)-enantiomer remained intact. Starting from both enantiomers ( approximately 70% ee) prepared by an established proline-mediated asymmetric Robinson annulation, the reduction with T. delbrueckii gave the (R)-enantiomer (98% ee) and the corresponding alcohol (4aS,5S)-4,4a, 5,6,7,8-hexahydro-5-hydroxy-4a-methyl-2(3H)-naphthalenone (94% ee, 94% de) in preparative scale in nearly quantitative yields. An approach for the asymmetric synthesis of the Wieland-Miescher ketone was also successful. 2-Methyl-2-(3-oxobutyl)-1,3-cyclohexanedione, the prochiral precursor, was reduced with this strain to give a cyclic acetal form of (2S, 3S)-3-hydroxy-2-methyl-2-(3-oxobutyl)cyclohexanone, in a stereomerically pure form.
38 citations
TL;DR: In this article, Imidazolidinones derived from the reaction of the catalyst and enamines have been found as intermediates in these reactions, and they have been shown to induce enantiomeric excesses in intramolecular aldol condensations.
38 citations
TL;DR: In this article, the authors used a silica-gel supported binam-derived prolinamides for the intramolecular and intermolecular aldol reaction under solvent-free conditions using conventional magnetic stirring.
36 citations
TL;DR: Ureas, carbamoyl derivatives, amides, and sulfonamides can be easily prepared from the strained (R,R)-cylohexanediamine urea in high yield, leaving a free amino group that shows good catalytic activity in intramolecular aldol condensations.
Abstract: Ureas, carbamoyl derivatives, amides, and sulfonamides can be easily prepared from the strained (R,R)-cylohexanediamine urea (1) in high yield, leaving a free amino group that shows good catalytic activity in intramolecular aldol condensations. The preparation of Wieland−Miescher ketone has been studied with these catalysts.
34 citations