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Design, Synthesis, and Application of Chiral C 2 ‐Symmetric Spiroketal‐Containing Ligands in Transition‐Metal Catalysis
Author(s) -
Argüelles Alonso J.,
Sun Siyuan,
Budaitis Brenna G.,
Nagorny Pavel
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201713304
Subject(s) - chemistry , palladium , catalysis , rhodium , transition metal , enantioselective synthesis , allylic rearrangement , iridium , stereoselectivity , dehydroalanine , combinatorial chemistry , asymmetric hydrogenation , stereochemistry , organic chemistry , amino acid , biochemistry
We present an expedient and economical route to a new spiroketal‐based C 2 ‐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 ).