Gold Catalysis, Asymmetric Friedel-Crafts Alkylation Cascade for One-Pot Synthesis of Chiral Dihydrocarbazoles and Dihydrodibenzofurans.
Org Lett
; 26(10): 2051-2056, 2024 Mar 15.
Article
in En
| MEDLINE
| ID: mdl-38436250
ABSTRACT
A one-pot gold-catalyzed acyl migration followed by ytterbium-catalyzed asymmetric Friedel-Crafts alkylation is disclosed, leading to the rapid synthesis of chiral dihydrocarbazoles and dihydrodibenzofuran in generally moderate to good overall yields with good to excellent enantioselectivities. The gold-catalyzed acyl migration of propargyl acetates generates α-ylidene-ß-diketones with high E/Z ratios, which are then subjected to the ytterbium-catalyzed asymmetric Friedel-Crafts alkylation without any purification. Importantly, this protocol provides a new type of substrate for asymmetric Friedel-Crafts alkylation.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2024
Document type:
Article
Affiliation country: