An asymmetric route to novel chiral cyclohexenones with spiro-connected cyclopentenes. Further utility of chiral bicyclic thiolactams and the (3,3) thio-Claisen products

Research was conducted to examine the asymmetric synthesis of diverse novel pirocyclic cyclohexonenes that include those bearing additional functionality. Results demonstrate that the sequential thio-Claisen rearrangement can be used to introduce two different allylic moieties in a diastereoselective fashion. Findings also show that the presence of functionality on the allylic bromide permits the rearrangement to proceed with a high degree of stereoselectivity.