Robustness screen in enantioselective catalysis enabled generation of enantioenriched heterocyclic scaffolds in one pot

TitleRobustness screen in enantioselective catalysis enabled generation of enantioenriched heterocyclic scaffolds in one pot
Publication TypeJournal Article
Year of Publication2015
AuthorsBagle, PN, Shinde, VS, Patil, NT
JournalChemistry-A European Journal
Volume21
Issue9
Pagination3580-3584
Date PublishedFEB
ISSN0947-6539
Keywordschiral Bronsted acid, Enantioselectivity, Gold, molecular scaffolds, robustness screen
Abstract

Enantioselective catalysis has emerged as a powerful synthetic paradigm and has accelerated the development of new methods to make diverse chiral molecules. Generally, these reactions are very sensitive to the steric and electronic environment present in the catalyst as well as the substrates. With this scenario, the presence of an additional component in the reaction mixture is expected to add complexity in achieving the enantioselective variants. Herein, we report that various enantioenriched molecules could be obtained from multiple starting materials in one pot. The reaction of aminoaromatics A with alkynols B-1, B-2, B-3...B-n with a Au-I/chiral BrOnsted acid catalyst afforded AB(1)*, AB(2)*, AB(3)*...AB(n)*; while, the reaction of alkynols B with aminoaromatics A(1), A(2), A(3)...A(n) under the same reaction conditions gave A(1)B*, A(2)B*, A(3)B*...A(n)B*.

DOI10.1002/chem.201406045
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)5.771
Divison category: 
Organic Chemistry