Design, Synthesis, and Application of Chiral C2 -Symmetric Spiroketal-Containing Ligands in Transition-Metal Catalysis

Alonso J Argüelles; Siyuan Sun; Brenna G Budaitis; Pavel Nagorny

doi:10.1002/anie.201713304

Design, Synthesis, and Application of Chiral C₂ -Symmetric Spiroketal-Containing Ligands in Transition-Metal Catalysis

Angew Chem Int Ed Engl. 2018 May 4;57(19):5325-5329. doi: 10.1002/anie.201713304. Epub 2018 Mar 23.

Authors

Alonso J Argüelles¹, Siyuan Sun¹, Brenna G Budaitis¹, Pavel Nagorny¹

Affiliation

¹ Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109, USA.

PMID: 29473275
DOI: 10.1002/anie.201713304

Abstract

We present an expedient and economical route to a new spiroketal-based C₂ -symmetric chiral scaffold, termed SPIROL. Based on this spirocyclic scaffold, several chiral ligands were generated. These ligands were successfully employed in an array of stereoselective transformations, including in iridium-catalyzed hydroarylations (up to 95 % ee), palladium-catalyzed allylic alkylations (up to 97 % ee), intermolecular palladium-catalyzed Heck couplings (up to 94 % ee), and rhodium-catalyzed dehydroalanine hydrogenation (up to 93 % ee).

Keywords: asymmetric catalysis; iridium; palladium; phosphines; spiroketals.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.