Directed ortho metallation of deep cavity cavitands: functionalizing molecular concavity

Zachary R Laughrey; Bruce C Gibb

doi:10.1021/jo0513515

Directed ortho metallation of deep cavity cavitands: functionalizing molecular concavity

J Org Chem. 2006 Feb 17;71(4):1289-94. doi: 10.1021/jo0513515.

Authors

Zachary R Laughrey¹, Bruce C Gibb

Affiliation

¹ Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, USA.

PMID: 16468774
DOI: 10.1021/jo0513515

Abstract

Directed ortho metallation (DOM) processes have been used to functionalize the cavity and rim of title cavitand 1. The preorganization of the host resulted in a considerable reduction in the range of products produced. Thus, whereas sixty-nine products are possible from per-functionalization, only twelve were observed when the host was treated with three different alkyllithiums.