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Enantioselective Dicarbofunctionalization of Unactivated Alkenes by Palladium-Catalyzed Tandem Heck/Suzuki Coupling Reaction
- Source :
- Angewandte Chemie (International ed. in English). 58(41)
- Publication Year :
- 2019
-
Abstract
- A highly enantioselective dicarbofunctionalization of unactivated alkenes was implemented by a Pd-catalyzed asymmetric tandem Heck/Suzuki coupling reaction. This reaction represents the first example of a highly enantioselective intramolecular cyclization/cross-coupling of olefin-tethered aryl halides with alkyl-, alkenyl- or arylboronic acids, and provides rapid access to a number of chiral compounds, such as dihydrobenzofurans, indolines, chromanes, and indanes bearing a quaternary stereocenter, in good yields with excellent enantioselectivities. The practicality of this reaction was validated in the modification of biologically complex molecules such as peptides, piperitol, CB2 receptor agonists, etc. Moreover, the synthesis of two enantiomers can be easily realized by simple change in the order of the steps in the coupling sequence.
- Subjects :
- chemistry.chemical_classification
Molecular Structure
010405 organic chemistry
Alkene
Aryl
Enantioselective synthesis
chemistry.chemical_element
General Chemistry
General Medicine
Alkenes
010402 general chemistry
01 natural sciences
Combinatorial chemistry
Catalysis
0104 chemical sciences
Stereocenter
chemistry.chemical_compound
chemistry
Suzuki reaction
Alkyl
Palladium
Subjects
Details
- ISSN :
- 15213773
- Volume :
- 58
- Issue :
- 41
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie (International ed. in English)
- Accession number :
- edsair.doi.dedup.....6784e17d6fbfc6efc3af0e7824eeb64f