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Org Lett. 2014 Jul 3;16(13):3421-3. doi: 10.1021/ol5012967. Epub 2014 Jun 13.

n→π* interactions engender chirality in carbonyl groups.

Author information

1
Graduate Program in Biophysics and Departments of ‡Chemistry and §Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.

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.

PMID:
24926562
PMCID:
PMC4096190
DOI:
10.1021/ol5012967
[Indexed for MEDLINE]
Free PMC Article

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