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Asymmetric induction through the use of remote covalent and ionic chiral auxiliaries in the solid state photochemistry of 2-benzoyladamantane-2-carboxylic acid derivatives

TitleAsymmetric induction through the use of remote covalent and ionic chiral auxiliaries in the solid state photochemistry of 2-benzoyladamantane-2-carboxylic acid derivatives
Publication TypeJournal Article
Year of Publication2000
AuthorsCheung, E, Netherton, MR, Scheffer, JR, Trotter, J, Zenova, A
JournalTetrahedron Letters
Volume41
Pagination9673-9677
Date PublishedDec
Type of ArticleArticle
ISBN Number0040-4039
KeywordsCRYSTALLINE STATE, YANG PHOTOCYCLIZATION REACTION
Abstract

Attachment of chiral auxiliaries to 2-benzoyladamantane-2-carboxylic acid, either covalently through ester formation with optically pure alcohols, or ionically via salt formation with optically pure amines, leads to substrates whose irradiation in the crystalline state affords chiral rearranged photoproducts in greater than or equal to 96% diastereo- and enantiomeric excess. (C) 2000 Elsevier Science Ltd. All rights reserved.
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