Enhanced enantio-and diastereoselectivity via confinement and cation binding: Yang photocyclization of 2-benzoyladamantane derivatives within zeolites

A Natarajan, A Joy, LS Kaanumalle…

Index: Natarajan, Arunkumar; Joy, Abraham; Kaanumalle, Lakshmi S.; Scheffer, John R.; Ramamurthy Journal of Organic Chemistry, 2002 , vol. 67, # 24 p. 8339 - 8350

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Citation Number: 18

Abstract

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 retro-aldol 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 ...