Journal
ACS CATALYSIS
Volume 8, Issue 4, Pages 2805-2809Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b04343
Keywords
C-N axial chirality; chiral iodanes; atropselective coupling; Cu-catalyzed coupling; sulfoxide
Categories
Funding
- CNRS (Centre National de la Recherche Scientifique)
- Ministere de l'Education Nationale et de la Recherche
- IcFRC, Strasbourg (International center of Frontier Research in Chemistry) France
- IcFRC, Strasbourg
- Ministere de l'Education Nationale et de la Recherche, France
Ask authors/readers for more resources
Axially chiral C-N compounds are an emerging but scarcely investigated class of stereogenic molecules with potential applications as biologically active scaffolds and chiral ligands. The synthesis of these compounds is extremely challenging, and in particular, no metal-catalyzed asymmetric, intermolecular C-N coupling has been previously reported. Herein we disclose an intermolecular atropselective C-N coupling, occurring with excellent stereoselectivity. This Cu-catalyzed transformation is based on the use of highly active coupling partners (i.e., chiral iodanes bearing a very cheap and traceless sulfoxide auxiliary). Use of such original ortho-sulfoxide iodanes enables this unprecedented coupling to occur at room temperature, guaranteeing high atropselectivity and atropselectivity of the coupling products under reaction conditions. Because of extensive possible postmodifications of the optically pure products, a panel of C-N axially chiral scaffolds can now be accessed.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available