Enantioselective Iron-Catalyzed Cross-[4+4]-Cycloaddition of 1,3-Dienes Provides Chiral Cyclooctadienes
Autor: | Elena Braconi, Nicolai Cramer, Alissa C Götzinger |
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Rok vydání: | 2020 |
Předmět: |
Steric effects
cyclodimerization metal Chemistry Iron catalyzed steering ligands Enantioselective synthesis mechanism General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry diene Catalysis Cycloaddition 0104 chemical sciences Colloid and Surface Chemistry asymmetric 1 4-addition Iron complex Reactivity (chemistry) Selectivity medium-sized rings cyclic olefins |
Zdroj: | Journal of the American Chemical Society. 142:19819-19824 |
ISSN: | 1520-5126 0002-7863 |
Popis: | Chiral cyclooctadienes are a frequently occurring scaffold in natural products and specialty chemicals, and are used as ligands in asymmetric catalysis. Accessing substituted cyclooctadienes in an efficient asymmetric fashion has been notoriously challenging. We report an iron-catalyzed enantioselective cross-[4+4]-cycloaddition of 1,3-dienes to form substituted cyclooctadienes under very mild conditions. A highly tailored chiral alpha-diimine iron complex is key for the success of the transformation providing a balanced performance between reactivity, excellent cross-selectivity and very high enantioselectivity. Steric maps of the complexes help accounting for the observed selectivity. The developed method allows rapid and atom-economic access to novel differently functionalized cyclooctadienes in very high yields and enantioselectivities. |
Databáze: | OpenAIRE |
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