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An ionic chiral auxiliary-induced regioselective and enantioselective Yang photocyclization reaction in the crystalline state

TitleAn ionic chiral auxiliary-induced regioselective and enantioselective Yang photocyclization reaction in the crystalline state
Publication TypeJournal Article
Year of Publication1999
AuthorsCheung, E, Kang, T, Raymond, JR, Scheffer, JR, Trotter, J
JournalTetrahedron Letters
Volume40
Pagination8729-8732
Date PublishedDec
Type of ArticleArticle
ISBN Number0040-4039
KeywordsASYMMETRIC INDUCTION, CARBOXYLATE, KETONES, ORGANIC-PHOTOCHEMISTRY, PHOTOCHEMISTRY, SOLID-STATE, Yang photocyclization
Abstract

cis-9-Decalyl aryl ketones undergo Yang photocyclization in solution to afford an approximately 1:1 mixture of two regioisomeric racemic cyclobutanols. In contrast, irradiation in the crystalline state in the presence of various ionic chiral auxiliaries leads to a single cyclobutanol in >98% enantiomeric excess. X-Ray crystallography reveals the source of the regio-, diastereo- and enantioselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.

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