4.7 Article

Diastereoselective Synthesis of Densely Functionalized 3a,8a-Dihydro-8H-furo[3,2-a]pyrrolizines through One-Pot Three-Component Assembly

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 17, Pages 12367-12377

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01315

Keywords

-

Funding

  1. National Research Foundation of Korea [NRF-2018R1A6A1A03023718, NRF-2020R1A2C2005961]

Ask authors/readers for more resources

The novel domino mode of assembly discovered in a one-pot three-component reaction under mild and eco-friendly conditions led to the synthesis of a new tricyclic skeleton, involving consecutive formation of multiple bonds and construction of two rings in a diastereoselective manner.
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.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available