Journal article
Chiral action at a distance: remote substituent effects on the optical activity of calyculins A and B
Organic letters, Vol.2(11), pp.1509-1512
06/01/2000
DOI: 10.1021/ol005634p
PMID: 10841466
Abstract
[structure--see text] Calyculins A and B differ only by the (E)- vs (Z)-configuration at C(2). Yet, they show a large difference in optical rotations. We demonstrate a new strategy that provides a physical analysis of this long-range chiro-optical effect by Boltzmann-averaged atomic contribution mapping. The polarizability characteristics of the CN substituent rather than the perturbation of the stereogenic centers or the introduction of asymmetry into the polyene chain give rise to the remarkable difference in rotation angles.
Details
- Title: Subtitle
- Chiral action at a distance: remote substituent effects on the optical activity of calyculins A and B
- Creators
- Ramu K Kondru - Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USADavid N BeratanGregory K FriestadAmos B Smith IIIPeter Wipf
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.2(11), pp.1509-1512
- Publisher
- United States
- DOI
- 10.1021/ol005634p
- PMID
- 10841466
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Grant note
- GM 55433-04 / NIGMS NIH HHS CA-19033 / NCI NIH HHS
- Language
- English
- Date published
- 06/01/2000
- Academic Unit
- Chemistry
- Record Identifier
- 9983985713402771
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