Synthesis, Optical Resolution, and Configurational Assignment of Novel Axially Chiral Quateraryls
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Goel, Atul
Singh, Fateh V Kumar, Vijay Reichert,Matthias Gulder, Tobias A M Bringmann, Gerhard |
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| Date |
2007-12-31T11:06:46Z
2007-12-31T11:06:46Z 2007 |
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| Identifier |
Journal of Organic Chemistry (2007), 72, 7765-68
http://hdl.handle.net/123456789/75 |
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| Description |
A one-pot, general synthesis of highly functionalized quateraryls through carbanion-induced, base-catalyzed ring transformation of 5,6-diaryl-2H-pyran-2-ones and core-substituted phenylacetones is delineated. These conversions were found to give diversely functionalized benzenes bearing peripheral aryl rings, some of which possess inherent atropisomerism. Exemplarily for one of the quateraryls, the optical resolution of the respective atropo-enantiomers by HPLC on a chiral phase and the assignment of their absolute axial configurations succeeded by LC-CD coupling in combination with semiempirical CNDO/S and TDDFT CD calculations. This synthetic approach offers – in a transition metal-free environment – high flexibility in the construction of quateraryls with the desired conformational freedom along the molecular axis, which may help in exploring and developing new potential ligands for asymmetric synthesis.
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| Format |
739618 bytes
application/pdf |
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| Language |
en
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| Relation |
CDRI Communication Number: 7203
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| Title |
Synthesis, Optical Resolution, and Configurational Assignment of Novel Axially Chiral Quateraryls
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| Type |
Article
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