@article {458,
	title = {Enhanced enantio- and diastereoselectivity via confinement and cation binding: Yang photocyclization of 2-benzoyladamantane derivatives within zeolites},
	journal = {Journal of Organic Chemistry},
	volume = {67},
	number = {24},
	year = {2002},
	note = {ISI Document Delivery No.: 620AATimes Cited: 5Cited Reference Count: 60},
	month = {Nov},
	pages = {8339-8350},
	type = {Article},
	abstract = {Irradiation of 2-benzoyladamantane derivatives in zeolites yields the endo-cyclobutanols as the only photoproduct via a gamma-hydrogen abstraction process. The cyclobutanols readily undergo retro-aldol reaction to give delta-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{\textquoteright}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 delta-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.},
	keywords = {ABSOLUTE ASYMMETRIC-SYNTHESIS, ACID-DERIVATIVES, CATALYSTS, COMPLEXES, EPOXIDATION, INDUCTION, PHOTOREACTIONS, SOLID-STATE, STATE ORGANIC-PHOTOCHEMISTRY, TROPOLONE ETHER},
	isbn = {0022-3263},
	url = {<Go to ISI>://000179509400006},
	author = {Natarajan, A. and Joy, A. and Kaanumalle, L. S. and Scheffer, J. R. and Ramamurthy, V.}
}
@article {5185,
	title = {2000 Alfred Bader Award Lecture - In the footsteps of Pasteur: asymmetric induction in the photochemistry of crystalline ammonium carboxylate salts},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {79},
	number = {4},
	year = {2001},
	note = {ISI Document Delivery No.: 429PNTimes Cited: 51Cited Reference Count: 52},
	month = {Apr},
	pages = {349-357},
	type = {Article},
	abstract = {This review describes the development of a new, synthetically useful method of asymmetric synthesis in organic photochemistry. Similar in many ways to the Pasteur procedure for resolving racemic carboxylic acids and organic amines, the method relies on the use of crystalline organic salts in which the enantioselectivity of a photochemical reaction of an achiral organic ion (for example, a carboxylate anion) is governed in the solid state by the presence of an optically pure counterion (for example, an optically active ammonium ion). Such optically pure counterions are termed ionic chiral auxiliaries. Salts containing ionic chiral auxiliaries are required to crystallize in chiral space groups, which provide the asymmetric environment necessary for chiral induction. Using this methodology, we have obtained near-quantitative optical yields in a wide variety of photochemical reactions.},
	keywords = {ABSOLUTE-CONFIGURATION CORRELATION, ACID-DERIVATIVES, asymmetric synthesis, chiral auxiliaries, crystal structure-reactivity relationships, di-pi-methane, GEOMETRIC REQUIREMENTS, II REACTION, ionic chiral auxiliaries, ORGANIC-PHOTOCHEMISTRY, PHOTOCHEMISTRY, solid state, SOLID-STATE PHOTOCHEMISTRY, STRUCTURE-REACTIVITY RELATIONSHIPS, YANG PHOTOCYCLIZATION REACTION},
	isbn = {0008-4042},
	url = {<Go to ISI>://000168526300001},
	author = {Scheffer, J. R.}
}
