Practical highly enantioselective synthesis of propargylamines through a copper-catalyzed one-pot three-component condensation reaction.
The one-pot three-component reaction of terminal alkynes, aldehydes and secondary amines in the presence of copper(I) bromide/quinap is reported. The reaction scope has been determined and a broad variety of all three components has been used, which afforded the corresponding propargylamines in good to excellent yields and moderate to very good enantioselectivities. The reaction showed a strong positive nonlinear effect. The transformation of a propargylamine intermediate into the alkaloid (S)-(+)-coniine has also been described.
Department Chemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, Haus F, 81377 München, Germany.
Nina
N
Gommermann
Paul
P
Knochel
D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011437:Propylamines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D000480:Alkynes; D000588:Amines; D001965:Bromides; D011437:Propylamines; C408079:cupric bromide; C009054:propargylamine; D003300:Copper; D010293:Pargyline