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Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C₂ -Symmetric Biaryls.

ABSTRACT: We have demonstrated that small, modular, tetrameric peptides featuring the Lewis-basic residue ?-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.

SUBMITTER: Coombs G

PROVIDER: S-EPMC7002259 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C<sub>2</sub> -Symmetric Biaryls.

Coombs Gavin G Sak Marcus H MH Miller Scott J SJ

Angewandte Chemie (International ed. in English) 20191230 7

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-C<sub>2</sub> -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.) enan ...[more]

PMID: 31793137

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