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Chiral Rhodium(III) Complex-Catalyzed Cascade Michael-Alkylation Reactions: Enantioselective Synthesis of Cyclopropanes
- Source :
- The Journal of Organic Chemistry. 82:796-803
- Publication Year :
- 2016
- Publisher :
- American Chemical Society (ACS), 2016.
-
Abstract
- Chiral Rh(III) complex catalyzed highly efficient enantioselective cyclopropanation of α,β-unsaturated 2-acyl imidazoles or pyridine with 2-bromomalonate is developed to generate corresponding multisubstituted cyclopropanes in 70-99% yields with 93→99% enantioselectivity. The proficiency of the process is also demonstrated in gram scale reaction maintaining same reactivity and selectivity level in lower catalyst loading. Moreover, the developed methodology is applicable in challenging synthesis of biscyclopropane scaffold with 97% ee in a single operation.
- Subjects :
- 010405 organic chemistry
Chemistry
Cyclopropanation
Organic Chemistry
Enantioselective synthesis
chemistry.chemical_element
Alkylation
010402 general chemistry
01 natural sciences
0104 chemical sciences
Rhodium
Catalysis
chemistry.chemical_compound
Pyridine
Organic chemistry
Reactivity (chemistry)
Selectivity
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 82
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....5240a091a64ee88e67bc527d246eb0c7