68157-27-7Relevant articles and documents
ELECTRON-TRANSFER INDUCED CONVERSION OF ENOL-ETHERS INTO KETONES
Lopez, Luigi,Troisi, Luigino
, p. 489 - 492 (1989)
Alkoxy (aryl)-methylidene adamantanes react with catalytic amounts of tris p-bromophenylammoniumyl hexachloroantimonate in CH2Cl2 under argon atmosphere, yielding adamantyl-arylketones together with the corresponding alcohols.The reaction most likely proc
Adamantylzinc bromides: Direct preparation and application to cross-coupling reaction
Hwang, Hyung-Seo,Joo, Seong-Ryu,Kim, Seung-Hoi
, p. 2769 - 2772 (2015/11/16)
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Enhanced enantio- and diastereoselectivity via confinement and cation binding: Yang photocyclization of 2-benzoyladamantane derivatives within zeolites
Natarajan, Arunkumar,Joy, Abraham,Kaanumalle, Lakshmi S.,Scheffer, John R.,Ramamurthy
, p. 8339 - 8350 (2007/10/03)
Irradiation of 2-benzoyladamantane derivatives in zeolites yields the endo-cyclobutanols as the only photoproduct via a γ-hydrogen abstraction process. The cyclobutanols readily undergo retroaldol reaction to give δ-ketoesters. The enantiomeric excess (ee) in the endo-cyclobutanols is measured by monitoring the ee in the ketoesters. Whereas in solution the ee in the product ketoester is zero, within achiral NaY zeolite, in the presence of a chiral inductor such as pseudoephedrine, ee's up to 28% have been obtained. The influence of zeolite on several chiral esters of 2-benzoyladamantane-2-carboxylic acids has also been examined. Whereas in solution the diastereomeric excess is 15%, in zeolite the δ-ketoesters are obtained in 79% de (best examples). Ab initio computations suggest that enhancement of chiral induction within zeolites is likely to be due to cation complexation with the reactant ketone. Alkali ion-organic interaction, a powerful tool, is waiting to be fully exploited in photochemical and thermal reactions. In this context zeolites could be a useful medium as one could view them as a reservoir of "naked" alkali ions that are only partially coordinated to the zeolite walls.