Pd(0)/InI-mediated allylic additions to 4-acetoxy-2-azetidinone: new route to highly functionalized carbocyclic scaffolds.

Cara Cesario, Marvin J Miller

Index: Org. Lett. 11(6) , 1293-5, (2009)

Full Text: HTML

Abstract

Acylnitroso-derived hetero-Diels-Alder cycloadducts are susceptible to C-O bond cleavage with Pd(0) and InI to form allylic indium(III) species. The in situ prepared allylindium compounds readily react at room temperature with Eschenmoser's salt. Allylation of 4-acetoxy-2-azetidinone provides derivatized cyclopentenes in high regio- and diastereoselectivity.