Diastereoselective Synthesis of Densely Functionalized 3a,8a-Dihydro-8H-furo[3,2-a]pyrrolizines through One-Pot Three-Component Assembly.
J Org Chem
; 86(17): 12367-12377, 2021 09 03.
Article
in En
| MEDLINE
| ID: mdl-34479403
ABSTRACT
A new domino mode of assembly was discovered from the one-pot three-component reactions of pyrrole derivatives, active methylene compounds (malononitrile, methyl cyanoacetate, or ethyl cyanoacetate), and sodium cyanide in the presence of piperidinium acetate in EtOH at room temperature, leading to a novel tricyclic skeleton in excellent yield under mild and eco-friendly conditions. This well-choreographed domino process enabled formation of multiple bonds (three C-C and one C-O) for consecutive construction of two rings (pyrrolidine and dihydrofuran) in a diastereoselective manner.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Pyrroles
Language:
En
Journal:
J Org Chem
Year:
2021
Type:
Article