title: Asymmetric vinylogous Michael reaction of cyclic enones with silyloxy furans.
abstract: The asymmetric vinylogous Michael reaction of cyclohexenone/medium and large cyclic enones with 2-silyloxyfuran is still a synthetic challenge. In this report, we have explored 1,4-conjugate addition of an enantioselective chiral, primary diamine catalyzed, 2-silyloxy furan to various cyclic enones and β-substituted cyclic enones. The reaction provided syn-Michael adducts (cycloalkane connected γ-butenolide) with good yields, diastereo and enantioselectivities. Furthermore, the synthetic potential of these syn-Michael adducts is demonstrated by 1,4-addition of nucleophiles on the butenolide substructure.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Delhi, Hauz Khas, New Delhi 110-016, India. ravips@chemistry.iitd.ac.in.
authors.forename: Amol P
authors.initials: AP
authors.lastname: Jadhav
authors.forename: V U
authors.initials: VU
authors.lastname: Bhaskara Rao
authors.forename: Pradeep
authors.initials: P
authors.lastname: Singh
authors.forename: R G
authors.initials: RG
authors.lastname: Gonnade
authors.forename: Ravi P
authors.initials: RP
authors.lastname: Singh
mesh_terms: D003512:Cyclohexanones / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D003512:Cyclohexanones; D005663:Furans; D014753:Vinyl Compounds; C036468:cyclohexanone