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Computational prediction of the enantioselectivity of a solid-state photoreaction

TitleComputational prediction of the enantioselectivity of a solid-state photoreaction
Publication TypeJournal Article
Year of Publication1999
AuthorsGarcia-Garibay, MA, Houk, KN, Keating, AE, Cheer, CJ, Leibovitch, M, Scheffer, JR, Wu, LC
JournalOrganic Letters
Volume1
Pagination1279-1281
Date PublishedOct
Type of ArticleArticle
ISBN Number1523-7060
KeywordsABSOLUTE ASYMMETRIC-SYNTHESIS, CRYSTAL LATTICES, FORCE-FIELD, MEDIA, MODEL, MOLECULAR MECHANICS, NUCLEIC-ACIDS, PHOTOCHEMISTRY, PROTEINS
Abstract

[GRAPHICS] To better understand the forces controlling chemical reactions in crystals, the absolute asymmetric photorearrangement of 4-m-chlorobenzyloxy-2-pyridone leading to the corresponding enantiomerically enriched (78% ee) beta-lactam was modeled computationally using a flexible minilattice consisting of a central reactant and 20 nearest and 72 next-nearest neighbors. The computational results predicted a preference for formation of the (R,R)-enantiomer, and this was verified experimentally by absolute configuration correlation studies.

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