Base-catalyzed intramolecular hydroamination of conjugated enynes.
A de novo intramolecular hydroamination of conjugated enynes was developed using commercially available n-BuLi as a precatalyst. This hydroamination reaction successfully afforded allenyl-substituted pyrrolidines with up to 95% yield. One of the resulting allenyl pyrrolidines was converted to the natural products irniine and irnidine in three steps.
Zhang
Wen
W
The School of Pharmacy and Department of Chemistry, University of Wisconsin, 777 Highland Avenue, Madison, Wisconsin 53705-2222, USA.
Werness
Jenny B
JB
Tang
Weiping
W
D000480:Alkynes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D009942:Organometallic Compounds; D011759:Pyrrolidines; C434823:n-butyllithium