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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201713304
Subject(s) - catalysis , palladium , chemistry , transition metal , rhodium , iridium , stereoselectivity , dehydroalanine , allylic rearrangement , combinatorial chemistry , enantioselective synthesis , stereochemistry , asymmetric hydrogenation , 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 ).