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.

SUBMITTER: Han C 

PROVIDER: S-EPMC2774802 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature