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Peptide‐Catalyzed Fragment Couplings that Form Axially Chiral Non‐ C 2 ‐Symmetric Biaryls
Author(s) -
Coombs Gavin,
Sak Marcus H.,
Miller Scott J.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201913563
Subject(s) - chemistry , yield (engineering) , naproxen , catalysis , stereochemistry , combinatorial chemistry , axial chirality , enantioselective synthesis , nonsteroidal , residue (chemistry) , peptide , organic chemistry , materials science , biochemistry , medicine , alternative medicine , pathology , metallurgy , pharmacology
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 2 ‐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.