Ren, Xinyi published the artcileAsymmetric Alkoxy- and Hydroxy-Carbonylations of Functionalized Alkenes Assisted by β-Carbonyl Groups, Application In Synthesis of 20880-92-6, the publication is Angewandte Chemie, International Edition (2021), 60(32), 17693-17700, database is CAplus and MEDLINE.
As a fundamental type of carbonylation reaction, the alkoxy- and hydroxy-carbonylation of unsaturated hydrocarbons constitutes one of the most important industrial applications of homogeneous catalysis. However, owing to the difficulties in controlling multi-selectivities for asym. hydrocarbonylation of alkenes, this reaction is typically limited to vinylarenes and analogs. In this work, a highly efficient asym. alkoxy- and hydroxy-carbonylation of β-carbonyl functionalized alkenes was developed, providing practical and easy access to various densely functionalized chiral mols. with high optical purity from broadly available alkenes, CO, and nucleophiles (>90 examples, 84-99% ee). This protocol features mild reaction conditions and a broad substrate scope, and the products can be readily transformed into a diverse array of chiral heterocycles. Control experiments revealed the key role of the β-carbonyl group in determining the enantioselectivity and promoting the activity, which facilitates chiral induction by coordination to the transition metal as rationalized by DFT calculations The strategy of utilizing an innate functional group as the directing group on the alkene substrate might find further applications in catalytic asym. hydrocarbonylation reactions.
Angewandte Chemie, International Edition published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H20O6, Application In Synthesis of 20880-92-6.
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