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- W4380874734 endingPage "13729" @default.
- W4380874734 startingPage "13715" @default.
- W4380874734 abstract "Alkene aminooxygenation and dioxygenation reactions that result in carbonyl products are uncommon, and protocols that control absolute stereochemistry are rare. We report herein catalytic enantioselective alkene aminooxygenation and dioxygenation that directly provide enantioenriched 2-formyl saturated heterocycles under aerobic conditions. Cyclization of substituted 4-pentenylsulfonamides, catalyzed by readily available chiral copper complexes and employing molecular oxygen as both oxygen source and stoichiometric oxidant, directly provides chiral 2-formyl pyrrolidines efficiently. Reductive or oxidative workup of these aldehydes provides their respective amino alcohols or amino acids (unnatural prolines). Enantioselective synthesis of an indoline and isoquinolines is also demonstrated. Concurrently, cyclization of various alkenols under similar conditions provides 2-formyl tetrahydrofurans, phthalans, isochromans, and morpholines. The nature of the copper ligands, the concentration of molecular oxygen, and the reaction temperature all impact the product distribution. Chiral nitrogen and oxygen heterocycles are common components of bioactive small molecules, and these enabling technologies provide access to saturated heterocycles functionalized with ready-to-use carbonyl electrophiles." @default.
- W4380874734 created "2023-06-17" @default.
- W4380874734 creator A5009453570 @default.
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- W4380874734 creator A5061360791 @default.
- W4380874734 creator A5069052319 @default.
- W4380874734 creator A5079810755 @default.
- W4380874734 date "2023-06-16" @default.
- W4380874734 modified "2023-10-16" @default.
- W4380874734 title "Copper-Catalyzed Enantioselective Aerobic Alkene Aminooxygenation and Dioxygenation: Access to 2-Formyl Saturated Heterocycles and Unnatural Proline Derivatives" @default.
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- W4380874734 doi "https://doi.org/10.1021/jacs.3c01985" @default.
- W4380874734 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/37327484" @default.
- W4380874734 hasPublicationYear "2023" @default.
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