title: Asymmetric alkynylation/lactamization cascade: an expeditious entry to enantiomerically enriched isoindolinones.
abstract: An unprecedented Cu(I)-pybox-diPh-catalyzed highly enantioselective (up to >99% ee) alkynylation/lactamization cascade has been developed as a general catalytic system for the synthesis of diversely substituted isoindolinones of immense biological importance. The cascade effects one C-C and two C-N bond-forming events in one reaction vessel under operationally simple, additive-free reaction conditions in good to excellent yields. The methodology was further extended to the synthesis of tetrahydroisoquinoline scaffolds common to several biologically active natural products in a two-step sequence with remarkable selectivity (up to 94% ee).
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal, M.P. - 462 066 (India); Indian Institute of Technology, Kanpur, U.P. - 208 016 (India).
authors.forename: Vishnumaya
authors.initials: V
authors.lastname: Bisai
authors.forename: Arun
authors.initials: A
authors.lastname: Suneja
authors.forename: Vinod K
authors.initials: VK
authors.lastname: Singh
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D007769:Lactams; D044005:Tetrahydroisoquinolines
keywords: alkynylation; domino reactions; isoindolinones; synthetic methods; tetrahydroisoquinolines