Chiral action at a distance: remote substituent effects on the optical activity of calyculins A and B.
Publication
, Journal Article
Kondru, RK; Beratan, DN; Friestad, GK; Smith, AB; Wipf, P
Published in: Organic letters
June 2000
[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.
Duke Scholars
Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
June 2000
Volume
2
Issue
11
Start / End Page
1509 / 1512
Related Subject Headings
- Vasoconstrictor Agents
- Thermodynamics
- Stereoisomerism
- Phosphoprotein Phosphatases
- Oxazoles
- Organophosphates
- Organic Chemistry
- Optical Rotation
- Molecular Conformation
- Models, Molecular
Citation
APA
Chicago
ICMJE
MLA
NLM
Kondru, R. K., Beratan, D. N., Friestad, G. K., Smith, A. B., & Wipf, P. (2000). Chiral action at a distance: remote substituent effects on the optical activity of calyculins A and B. Organic Letters, 2(11), 1509–1512. https://doi.org/10.1021/ol005634p
Kondru, R. K., D. N. Beratan, G. K. Friestad, A. B. Smith, and P. Wipf. “Chiral action at a distance: remote substituent effects on the optical activity of calyculins A and B.” Organic Letters 2, no. 11 (June 2000): 1509–12. https://doi.org/10.1021/ol005634p.
Kondru RK, Beratan DN, Friestad GK, Smith AB, Wipf P. Chiral action at a distance: remote substituent effects on the optical activity of calyculins A and B. Organic letters. 2000 Jun;2(11):1509–12.
Kondru, R. K., et al. “Chiral action at a distance: remote substituent effects on the optical activity of calyculins A and B.” Organic Letters, vol. 2, no. 11, June 2000, pp. 1509–12. Epmc, doi:10.1021/ol005634p.
Kondru RK, Beratan DN, Friestad GK, Smith AB, Wipf P. Chiral action at a distance: remote substituent effects on the optical activity of calyculins A and B. Organic letters. 2000 Jun;2(11):1509–1512.
Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
June 2000
Volume
2
Issue
11
Start / End Page
1509 / 1512
Related Subject Headings
- Vasoconstrictor Agents
- Thermodynamics
- Stereoisomerism
- Phosphoprotein Phosphatases
- Oxazoles
- Organophosphates
- Organic Chemistry
- Optical Rotation
- Molecular Conformation
- Models, Molecular