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Asymmetric induction in the solid state photochemistry of an alpha-mesitylacetophenone derivative through the use of ionic chiral auxiliaries

TitleAsymmetric induction in the solid state photochemistry of an alpha-mesitylacetophenone derivative through the use of ionic chiral auxiliaries
Publication TypeJournal Article
Year of Publication1999
AuthorsCheung, E, Rademacher, K, Scheffer, JR, Trotter, J
JournalTetrahedron Letters
Volume40
Pagination8733-8736
Date PublishedDec
Type of ArticleArticle
ISBN Number0040-4039
KeywordsASYMMETRIC INDUCTION, CARBOXYLATE, CRYSTAL, KETONES, PHOTOCHEMISTRY, REARRANGEMENTS
Abstract

Irradiation in the crystalline state of salts formed between alpha-mesitylacetophenone-p-carboxylic acid and a variety of optically pure amines - the so-called ’ionic chiral auxiliary’ approach to asymmetric synthesis - leads to the corresponding 2-indanol in excellent yield and in high enantiomeric excess. X-Ray crystallography reveals the source of the enantioselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.
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