Alkyl groups on the metal enhance the reactivity of the 'classical' zirconium enolate of 1-methoxycyclohexanone

Article abstract of DOI:10.1016/0957-4166(96)00402-8

Compound 2 is the key intermediate in the preparation of our lead trinem antibiotic sanfetrinem 1a. In this communication it is described how a modified 'Evans' zirconium enolate of 1-methoxycyclohexanone is able to react with acetidinone 3 in the presence of LiHMDS under strict kinetic conditions, giving 2 with good yield and selectivity. Copyright (C) Elsevier Science Ltd.