Diastereoselective synthesis of pyrrolidines via the Yb(OTf)3 catalyzed three-component reaction of aldehydes, amines, and 1,1-cyclopropanediesters.
[Chemical reaction: see text] Aldimines, generated in situ by the reaction of primary amines or anilines with aldehydes, undergo smooth reaction with various 1,1-cyclopropanediesters in the presence of catalytic Yb(OTf)3. The products are pyrrolidines in which the major diastereomer bears a cis relationship between substituents at the 2- and 5-positions. In most cases the diastereoselectivity is greater than 10:1.
Carson
Cheryl A
CA
Department of Chemistry, University of Western Ontario, London, Ontario, Canada, N6A 5B7.
Kerr
Michael A
MA
D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry*
D000447:Aldehydes; D000588:Amines; D003521:Cyclopropanes; D007202:Indicators and Reagents; D011759:Pyrrolidines