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α-Alkylation and Asymmetric Transfer Hydrogenation of Tetralone via Hydrogen Borrowing and Dynamic Kinetic Resolution Strategy Using a Single Iridium(III) Complex.

Seung Wook KimElizabeth A FokerWilliam J WolfRyan A WoltornistAndrii ShemetShelby McCowenEric M SimmonsZiqing LinBrian L HeRobert MengerXuejun XuSloan AyersMatthew H BunnerAmy A Sarjeant
Published in: Organic letters (2024)
Here we present a novel strategy for the synthesis of enantiomerically enriched tetrahydronaphthalen-1-ols. The reaction proceeds via an alkylation (via hydrogen borrowing) and ammonium formate-mediated asymmetric transfer hydrogenation (via dynamic kinetic resolution), giving alkylated tetralols in high yields and good enantio- and diastereoselectivity across a diverse range of both alcohol and tetralone substrates. Additionally, these products were successfully derivatized to several complex molecules, demonstrating the utility of the tetrahydronaphthalen-1-ol.
Keyphrases
  • single molecule
  • electron transfer
  • ionic liquid
  • alcohol consumption
  • visible light