Desymmetrization of meso-Bicyclic Hydrazines: An Efficient Strategy towards the Synthesis of Functionalized Cyclopentenes

Abstract

Desymmetrization of meso-bicyclic hydrazines offers a facile entry into the class of functionalized cyclopentenes. Various methodologies used along this direction are described in this account. Our attempts in this area proved that the palladium-catalyzed desymmetrization of these substrates with various organometallic reagents results in the formation of 3,4-disubstituted cyclopentenes.

Diastereoselective Ring Homologation of Bicyclic Hydrazines: Access to cis-1,3-Diaminocyclohexitols

“…3 In this context, our group has been involved in the synthesis of polysubstituted 1,3-diamino cyclopentanes 3 (4) or piperidines 4 (5) starting from bicyclic hydrazine 5 . 6 Herein, we wish to report a straightforward and fully stereoselective approach toward hydroxylated 1,3-di- and 1,3,5-triaminocyclohexanes from a single precursor.…”