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- Title
Copper‐Complex‐Catalyzed Asymmetric Aerobic Oxidative Cross‐Coupling of 2‐Naphthols: Enantioselective Synthesis of 3,3′‐Substituted C<sub>1</sub>‐Symmetric BINOLs.
- Authors
Tian, Jin‐Miao; Wang, Ai‐Fang; Yang, Ju‐Song; Zhao, Xiao‐Jing; Tu, Yong‐Qiang; Zhang, Shu‐Yu; Chen, Zhi‐Min
- Abstract
A novel chiral 1,5‐N,N‐bidentate ligand based on a spirocyclic pyrrolidine oxazoline backbone was designed and prepared, and it coordinates CuBr in situ to form an unprecedented catalyst that enables efficient oxidative cross‐coupling of 2‐naphthols. Air serves as an external oxidant and generates a series of C1‐symmetric chiral BINOL derivatives with high enantioselectivity (up to 99 % ee) and good yield (up to 87 %). This approach is tolerant of a broader substrates scope, particularly substrates bearing various 3‐ and 3′‐substituents. A preliminary investigation using one of the obtained C1‐symmetric BINOL products was used as an organocatalyst, exhibiting better enantioselectivity than the previously reported organocatalyst, for the asymmetric α‐alkylation of amino esters.
- Subjects
BINAPHTHOL; ESTERS; SPINE; DIALKYLZINC; OXIDIZING agents; CATALYSTS
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 32, p11139
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201903435