Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C2-Symmetric Biaryls
Gavin Coombs
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT, 06511 USA
Search for more papers by this authorMarcus H. Sak
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT, 06511 USA
Search for more papers by this authorCorresponding Author
Prof. Scott J. Miller
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT, 06511 USA
Search for more papers by this authorGavin Coombs
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT, 06511 USA
Search for more papers by this authorMarcus H. Sak
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT, 06511 USA
Search for more papers by this authorCorresponding Author
Prof. Scott J. Miller
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT, 06511 USA
Search for more papers by this authorAbstract
We have demonstrated that small, modular, tetrameric peptides featuring the Lewis-basic residue β-dimethylaminoalanine (Dmaa) are capable of atroposelectively coupling naphthols and ester-bearing quinones to yield non-C2-symmetric BINOL-type scaffolds with good yields and enantioselectivity. The study culminates in the asymmetric synthesis of backbone-substituted scaffolds similar to 3,3′-disubstituted BINOLs, such as (R)-TRIP, with good (94:6 e.r.) to excellent (>99.9:0.1 e.r.) enantioselectivity after recrystallization, and a diastereoselective net arylation of the minimally modified nonsteroidal anti-inflammatory drug (NSAID) naproxen.
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