NDLI: Monitoring reaction centers and molecules during an enantioselective photoreaction in a crystal

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Crystal engineering with ethynylbenzenesPart 2. Structures of 4-trimethylsilylethynyl-N,N-dimethylaniline, and 4-ethynyl-N,N-dimethylaniline with Z′= 12 and a single-crystal to single-crystal phase transition at 122.5 ± 2 K

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Monitoring reaction centers and molecules during an enantioselective photoreaction in a crystal

Content Provider	Royal Society of Chemistry (RSC)
Author	Xia, Wujiong Bąkowicz, Julia Turowska-Tyrk, Ilona Scheffer, John R.
Copyright Year	2006
Abstract	The single crystal-to-single crystal retro-Claisen photorearrangement of the salt of 7-(4-carboxybenzoyl)norbornene with (S)-(−)-1-cyclohexylethylamine was studied. Although this reaction is an ionic chiral auxiliary-mediated asymmetric synthesis, which normally affords highly enantio-enriched products, the enantiomeric excess in this case is a relatively low 60% (80% of one enantiomer, 20% of the other). X-ray structure analysis was used in order to describe changes in the reaction centers and the behavior of molecules during the photoreaction and to understand the formation of two enantiomers. It was discovered that the conformation of the reactant molecules changes during the photoreaction to one that enables the formation of the minor enantiomer. This was seen clearly at ca. 30% reaction progress. The variations in the cell constants as a function of reaction progress are also presented. The structural changes taking place during the retro-Claisen photorearrangement are compared to the changes observed for other intra- and intermolecular photoreactions in crystals.
Starting Page	616
Ending Page	621
Page Count	6
File Format	HTM / HTML PDF
ISSN	14668033
Volume Number	8
Issue Number	8
Journal	CrystEngComm
DOI	10.1039/b607425a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	X-ray crystallography Chirality Enantiomer Conformational isomerism Enantiomeric excess Norbornene Enantioselective synthesis
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics Materials Science

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