Ultrafast iron-catalyzed reduction of functionalized ketones

• Verfasst von: Blasius, Clemens K. [VerfasserIn]
• Verfasst von: Vasilenko, Vladislav [VerfasserIn]
• Verfasst von: Gade, Lutz H. [VerfasserIn]
• Titel: Ultrafast iron-catalyzed reduction of functionalized ketones
• Titelzusatz: highly enantioselective synthesis of halohydrines, oxaheterocycles, and aminoalcohols$ddedicatedvto Professor Dietmar Stalke on the occasion of his 60th birthday
• Gefeierte Person: Stalke, Dietmar [GefeierteR]
• Verf.angabe: Clemens K. Blasius, Vladislav Vasilenko, and Lutz H. Gade
• E-Jahr: 2018
• Jahr: July 11, 2018
• Umfang: 5 S.
• Fussnoten: Gesehen am 13.09.2019
• Titel Quelle: Enthalten in: Angewandte Chemie / International edition
• Ort Quelle: Weinheim : Wiley-VCH, 1962
• Jahr Quelle: 2018
• Band/Heft Quelle: 57(2018), 32, Seite 10231-10235
• ISSN Quelle: 1521-3773
• DOI: doi:10.1002/anie.201806196
• Datenträger: Online-Ressource
• Dokumenttyp: Festschrift
• Sprache: eng
• Sach-SW: amino alcohols
• Sach-SW: enantioselectivity
• Sach-SW: hydroboration
• Sach-SW: iron
• Sach-SW: ligand design
• K10plus-PPN: 1676917373

Abstract

A molecularly defined chiral boxmi iron alkyl complex catalyzes the hydroboration of various functionalized ketones and provides the corresponding chiral halohydrines, oxaheterocycles (oxiranes, oxetanes, tetrahydrofurans, and dioxanes) and amino alcohols with excellent enantioselectivities (up to >99 %ee) and conversion efficiencies at low catalyst loadings (as low as 0.5 mol %). Turnover frequencies of greater than 40000 h−1 at −30 °C highlight the activity of this earth-abundant metal catalyst which tolerates a large number of functional groups.