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Preparation of Optically Active cis-Cyclopropane Carboxylates: Cyclopropanation of α-Silyl Stryenes with Aryldiazoacetates and Desilylation of the Resulting Silyl Cyclopropanes
- Source :
- Organic letters. 18(17)
- Publication Year :
- 2016
-
Abstract
- Optically active cis-cyclopropane carboxylates are prepared via the Rh2(S-PTAD)4-catalyzed cyclopropanation of α-silyl styrenes with aryl diazoacetates followed by desilylation of the resulting silyl cyclopropane carboxylates. The conjugation of the aryl ring with C═C bond and π stacking are proposed for the stereoselectivity of cyclopropanation, and configuration inversion is observed with the desilylation process.
- Subjects :
- Silylation
010405 organic chemistry
Cyclopropanation
Stereochemistry
Aryl
Organic Chemistry
Stacking
Optically active
010402 general chemistry
Ring (chemistry)
01 natural sciences
Biochemistry
Medicinal chemistry
0104 chemical sciences
Cyclopropane
chemistry.chemical_compound
chemistry
Stereoselectivity
Physical and Theoretical Chemistry
Subjects
Details
- ISSN :
- 15237052
- Volume :
- 18
- Issue :
- 17
- Database :
- OpenAIRE
- Journal :
- Organic letters
- Accession number :
- edsair.doi.dedup.....6acdba4b6d88f448a3a1683ccfdc66ed