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Linearly conjugated benzocyclohexadienone photochemistry in the solid state: ionic chiral auxiliary mediated asymmetric induction

TitleLinearly conjugated benzocyclohexadienone photochemistry in the solid state: ionic chiral auxiliary mediated asymmetric induction
Publication TypeJournal Article
Year of Publication1999
AuthorsCheung, E, Netherton, MR, Scheffer, JR, Trotter, J
JournalTetrahedron Letters
Volume40
Pagination8737-8740
Date PublishedDec
Type of ArticleArticle
ISBN Number0040-4039
KeywordsASYMMETRIC INDUCTION, KETONES, PHOTOCHEMISTRY, REARRANGEMENT, [pi(a)(2)+sigma(a)(2)]
Abstract

Asymmetric induction in the photochemistry of a linearly conjugated benzocyclohexadienone derivative has been achieved for the first time through the use of the solid state ionic chiral auxiliary method. Enantiomeric excesses as high as 70-80% at reasonable conversions are readily attainable. Crystal structures for both reactant and product are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.
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