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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4096190 | PMC |
| http://dx.doi.org/10.1021/ol5012967 | DOI Listing |
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