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

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...

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Veröffentlicht in:Organic letters 2024-04, Vol.26 (15), p.3103-3108
Hauptverfasser: Kim, Seung Wook, Foker, Elizabeth A., Wolf, William J., Woltornist, Ryan A., Shemet, Andrii, McCowen, Shelby, Simmons, Eric M., Lin, Ziqing, He, Brian L., Menger, Robert, Xu, Xuejun, Ayers, Sloan, Bunner, Matthew H., Sarjeant, Amy A.
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Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c00718