title: Cu(I)-catalyzed tandem benzyldiazoester coupling with terminal alkyne-allene formation-Michael reaction: application to the syntheses of oxa and azacycles.
abstract: A simple and practical procedure for the synthesis of aza- and oxacycles, which possess an array of stereogenic functionalities, is described. This protocol relies on tandem Cu-catalyzed coupling of suitably functionalized terminal alkyne with diazoester followed by isomerization and subsequent aza or oxa-Michael reaction, thus generating the required scaffold with high diastereoselectivity.
authors.affiliation: Organic Division III, Indian Institute of Chemical Technology, Hyderabad, 500 607, India. gkswamy_iict@yahoo.co.in
authors.forename: Gullapalli
authors.initials: G
authors.lastname: Kumaraswamy
authors.forename: Neerasa
authors.initials: N
authors.lastname: Jayaprakash
authors.forename: Guniganti
authors.initials: G
authors.lastname: Balakishan
mesh_terms: D000466:Alkadienes / Q000032:analysis / Q000138:chemical synthesis*; D000480:Alkynes / Q000032:analysis / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D000480:Alkynes; D001372:Aza Compounds; D004952:Esters; C025947:propadiene; D003300:Copper