Asymmetric Weitz-Scheffer epoxidation of isoflavones with hydroperoxides mediated by optically active phase-transfer catalysts was written by Adam, Waldemar;Rao, Paraselli Bheema;Degen, Hans-Georg;Levai, Albert;Patonay, Tamas;Saha-Moeller, Chantu R.. And the article was included in Journal of Organic Chemistry in 2002.Related Products of 69221-14-3 This article mentions the following:
The asym. Weitz-Scheffer epoxidation of the isoflavones I (R5 = H, Me, Et, Me2CH, R6 = H, MeO, R7 = Me, MeSO2), mediated by cinchonine- and cinchonidine-derived phase-transfer catalysts (PTCs), affords the corresponding enantiomerically enriched isoflavone epoxides with ee values of up to 98% in nearly quant. yields. With the appropriately configured PTC, both enantiomers of the isoflavone epoxides may be obtained by using the com. available cumyl hydroperoxide as oxidant. Methylation of the hydroxy functionality in the most effective PTC reduces significantly the enantioselectivity of the isoflavone epoxidation as illustrated for the substrate I (R5 = Et, R6 = H, R7 = Me). This fact indicates the pivotal role of the hydroxy group for enantioselective control, which is rationalized in terms of a hydrogen-bonded aggregate between the ether-oxygen atom of isoflavone I and the phase-transfer catalyst. The present attractive and convenient method should be useful for the preparation of optically active epoxides of the biol. relevant isoflavone structure. In the experiment, the researchers used many compounds, for example, (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3Related Products of 69221-14-3).
(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3) belongs to quinuclidine derivatives. Quinuclidine is found as a structural component of some biomolecules including quinine. As a ligand, quinuclidine is useful in the studies of OsO4-catalyzed dihydroxylation of olefins. It plays an important role in the formation of onium salts used testing of PAC-antagonist activity.Related Products of 69221-14-3
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider