n→π* interactions engender chirality in carbonyl groups.
Org Lett
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| Abstract | An n→π* interaction stems from the delocalization of the electron pair (n) of a donor group into the antibonding orbital (π*) of a carbonyl group. Crystallographic analyses of five pairs of diastereoisomers demonstrate that an n→π* interaction can induce chirality in an otherwise planar, prochiral carbonyl group. Thus, a subtle delocalization of electrons can have stereochemical consequences. |
| Year of Publication | 2014
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| Journal | Org Lett
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| Volume | 16
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| Issue | 13
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| Pages | 3421-3
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| Date Published | 2014 Jul 03
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| ISSN | 1523-7052
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| DOI | 10.1021/ol5012967
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| PubMed ID | 24926562
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| PubMed Central ID | PMC4096190
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| Grant list | R01 AR044276 / AR / NIAMS NIH HHS / United States
T32 GM008349 / GM / NIGMS NIH HHS / United States
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