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Iridium-Catalyzed Diastereo-, Enantio-, and Regioselective Allylic Alkylation with Prochiral Enolates
- Source :
- ACS Catalysis. 6:6207-6213
- Publication Year :
- 2016
- Publisher :
- American Chemical Society (ACS), 2016.
-
Abstract
- Transition-metal-catalyzed asymmetric allylic alkylation of enolates is a powerful method for the formation of carbon− carbon bonds. Within this field, palladium-catalyzed allylic alkylation reactions have undoubtedly been the most studied. Aside from limited cases, palladium catalysts preferentially form the linear substitution product through alkylation at the less-substituted terminus of the allylic electrophile (Scheme 1). However, in contrast to palladium, most other transition metals (e.g., Mo, W, Fe, Ru, Co, Rh, Ni, Pt, and Ir) have been shown to favor the construction of the branched product, with iridium catalysts being some of the most efficient and selective. The potential application of these chiral, branched products to the synthesis of natural products and biologically active compounds has motivated the development of practical and reliable transition-metal-catalyzed methods for their construction.
- Subjects :
- Allylic rearrangement
010405 organic chemistry
chemistry.chemical_element
Regioselectivity
General Chemistry
Alkylation
010402 general chemistry
01 natural sciences
Combinatorial chemistry
Article
Catalysis
0104 chemical sciences
Tsuji–Trost reaction
chemistry
Electrophile
Organic chemistry
Iridium
Palladium
Subjects
Details
- ISSN :
- 21555435
- Volume :
- 6
- Database :
- OpenAIRE
- Journal :
- ACS Catalysis
- Accession number :
- edsair.doi.dedup.....93f6accd0a6b1197b7815d6ff3caf814