title: Reaction discovery employing macrocycles: transannular cyclizations of macrocyclic bis-lactams.
abstract: Macrocyclic bis-lactams have been synthesized by cyclodimerization of homoallylic amino esters employing a Zr(IV)-catalyzed ester-amide exchange protocol. Base-mediated transannular cyclizations have been identified to access both bicyclic [5-11] and tricyclic [5-8-5] frameworks in good yield and diastereoselectivity. Preliminary mechanistic studies support an olefin isomerization-intramolecular conjugate addition pathway.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
authors.forename: Chong
authors.initials: C
authors.lastname: Han
authors.forename: Sathish
authors.initials: S
authors.lastname: Rangarajan
authors.forename: Alicia C
authors.initials: AC
authors.lastname: Voukides
authors.forename: Aaron B
authors.initials: AB
authors.lastname: Beeler
authors.forename: Richard
authors.initials: R
authors.lastname: Johnson
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D003500:Cyclization; D007700:Kinetics; D007769:Lactams / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D047028:Macrocyclic Compounds