title: Build/couple/pair strategy combining the Petasis 3-component reaction with Ru-catalyzed ring-closing metathesis and isomerization.
abstract: A "build/couple/pair" pathway for the systematic synthesis of structurally diverse small molecules is presented. The Petasis 3-component reaction was used to synthesize anti-amino alcohols displaying pairwise reactive combinations of alkene moieties. Upon treatment with a ruthenium alkylidene-catalyst, these dienes selectively underwent ring-closing metathesis reactions to form 5- and 7-membered heterocycles and cyclic aminals via a tandem isomerization/N-alkyliminium cyclization sequence.
authors.forename: Erhad
authors.initials: E
authors.lastname: Ascic
authors.forename: Sebastian T
authors.initials: ST
authors.lastname: Le Quement
authors.forename: Mette
authors.initials: M
authors.lastname: Ishoey
authors.forename: Mathilde
authors.initials: M
authors.lastname: Daugaard
authors.forename: Thomas E
authors.initials: TE
authors.lastname: Nielsen
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000588:Amines; D000605:Amino Alcohols; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D012428:Ruthenium