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Chiral Action at a Distance: Remote Substituent Effects on the Optical Activity of Calyculins A and B

Kondru, RK and Beratan, DN and Friestad, GK and Smith, AB and 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. ISSN 1523-7060

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(Equation Presented) 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 dissymmetry into the polyene chain give rise to the remarkable difference in rotation angles.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Kondru, RK
Beratan, DN
Friestad, GK
Smith, AB
Wipf, Ppwipf@pitt.eduPWIPF
Date: 1 June 2000
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 2
Number: 11
Page Range: 1509 - 1512
DOI or Unique Handle: 10.1021/ol005634p
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Biological Factors--chemistry; Carcinogens--chemistry; Enzyme Inhibitors--chemistry; Models, Molecular; Molecular Conformation; Optical Rotation; Organophosphates--chemistry; Oxazoles--chemistry; Phosphoprotein Phosphatases--antagonists & inhibitors; Stereoisomerism; Thermodynamics; Vasoconstrictor Agents--chemistry
PubMed ID: 10841466
Date Deposited: 21 Feb 2014 21:09
Last Modified: 02 Aug 2020 13:57


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