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A Theoretical Rationalization of the Asymmetric Induction in Sulfinyl-Directed [5C + 2c] Intramolecular Cycloadditions.
- Source :
-
Journal of Organic Chemistry . 12/12/2003, Vol. 68 Issue 25, p9780-9786. 7p. 16 Diagrams, 9 Charts, 3 Graphs. - Publication Year :
- 2003
-
Abstract
- A computational DFT examination (B3LYP/6-31G* and B3LYP/6-311+G**//B3LYP/6-31G*) of the thermal [5C + 2C] cycloaddditions of 6-acetoxy-3-pyranones and 3-silyloxy-4-pyrones with tethered alkenyl sulfoxides confirms that the high level of diastereofacial selectivity obtained is ultimately due to the preference of the alkenesulfinyl group to adopt a well-defined conformation in the transition state of the reaction. This conformation, which is different from that found in the ground state, is most probably dictated by dipolar interaction effects between the sulfoxide and the oxidopyrylium ylide intermediate. [ABSTRACT FROM AUTHOR]
- Subjects :
- *RING formation (Chemistry)
*CHEMISTRY
*ORGANIC chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 68
- Issue :
- 25
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 11838919
- Full Text :
- https://doi.org/10.1021/jo035259p