title: Catalytic Synthesis of N-Unprotected Piperazines, Morpholines, and Thiomorpholines from Aldehydes and SnAP Reagents.
abstract: Commercially available SnAP (stannyl amine protocol) reagents allow the transformation of aldehydes and ketones into a variety of N-unprotected heterocycles. By identifying new ligands and reaction conditions, a robust catalytic variant that expands the substrate scope to previously inaccessible heteroaromatic substrates and new substitution patterns was realized. It also establishes the basis for a catalytic enantioselective process through the use of chiral ligands.
authors.affiliation: Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zurich, Vladimir-Prelog-Weg 3, 8093 Zurich (Switzerland) http://www.bode.ethz.ch.
authors.forename: Michael U
authors.initials: MU
authors.lastname: Luescher
authors.affiliation: Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zurich, Vladimir-Prelog-Weg 3, 8093 Zurich (Switzerland) http://www.bode.ethz.ch. bode@org.chem.ethz.ch.
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents / Q000737:chemistry*; D009025:Morpholines / Q000138:chemical synthesis*; D010879:Piperazines / Q000138:chemical synthesis*; D014001:Tin / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D007202:Indicators and Reagents; D009025:Morpholines; D010879:Piperazines; D014001:Tin
keywords: SnAP reagents; aldehydes; cross-coupling; homogeneous catalysis; nitrogen heterocycles