Scope and mechanistic investigations of Pd-catalyzed coupling/cyclizations and cycloisomerizations of allenyl malonates.

ABSTRACT: Pd-catalyzed transformations of allenyl malonates provide convenient access to functionalized carbocycles, but the influence of the ligand, solvent, base, and reaction conditions on the mechanism, regioselectivity, and product outcome of the cyclization are not well-understood. Additionally, from the perspective of synthetic utility, access to either fully substituted or enantioenriched cyclopentane building blocks has not yet been achieved. This work describes how targeted changes to the reaction conditions enable predictable control over the mechanism of Pd-catalyzed allene cross-coupling/cyclization and cycloisomerization, irrespective of the allene substitution pattern. Both enantioenriched cyclopropanes and cyclopentenes can be obtained through axis-to-center chirality transfer from t

SUBMITTER: Vine LE 

PROVIDER: S-EPMC9275122 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature