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Molecular mechanics-assisted crystal engineering of solid state photoreactions: application to the Yang photocyclization of alpha-1-norbornylacetophenone derivatives

TitleMolecular mechanics-assisted crystal engineering of solid state photoreactions: application to the Yang photocyclization of alpha-1-norbornylacetophenone derivatives
Publication TypeJournal Article
Year of Publication2005
AuthorsBotoshansky, M, Braga, D, Kaftory, M, Maini, L, Patrick, BO, Scheffer, JR, Wang, KY
JournalTetrahedron Letters
Volume46
Pagination1141-1144
Date PublishedFeb
Type of ArticleArticle
ISBN Number0040-4039
KeywordsASYMMETRIC INDUCTION, crystal engineering, GEOMETRIC REQUIREMENTS, II REACTION, ionic chiral auxiliaries, REACTIVITY, solid state photochemistry, X-RAY CRYSTALLOGRAPHY, Yang photocyclization
Abstract

Based on molecular mechanics, Yang photocyclization of alpha-1-norbornylacetophenone derivatives in the crystalline state was engineered through methylation adjacent to the carbonyl group, thus changing the conformation in the crystal and leading to enhanced diastereo- and enantioselectivity. (C) 2004 Elsevier Ltd. All rights reserved.
URL<Go to ISI>://000226846800021