Source:http://linkedlifedata.com/resource/pubmed/id/15755178
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
10
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| pubmed:dateCreated |
2005-3-9
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| pubmed:abstractText |
Gamma-hydrogen abstraction has been revealed to be the primary photoprocess in the crystalline state of alpha-oxoamides through photochemical and X-ray structural studies. The outstanding ability of a covalent chiral auxiliary in generating asymmetric induction in the photoproduct beta-lactam has been established with 10 examples. We have shown that the crystal lattice preorganizes the reactant molecules toward a single diastereomer of the beta-lactam and prevents large motions of the 1,4-diradical intermediate that would result in the loss of stereochemical memory. A rare single-crystal-to-single-crystal transformation path of one of the examples investigated establishes the direct correlation between the stereochemistries of the reactant and the product.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
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| pubmed:month |
Mar
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| pubmed:issn |
0002-7863
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| pubmed:author | |
| pubmed:issnType |
Print
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| pubmed:day |
16
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| pubmed:volume |
127
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
3568-76
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| pubmed:year |
2005
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| pubmed:articleTitle |
Asymmetric induction during Yang cyclization of alpha-oxoamides: the power of a covalently linked chiral auxiliary is enhanced in the crystalline state.
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| pubmed:affiliation |
Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, USA.
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| pubmed:publicationType |
Journal Article
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