106753-93-9Relevant academic research and scientific papers
Model Studies on the Synthesis of Medium-sized and Large Carbocycles using the Ireland Enolate Claisen Rearrangement
Cameron, Andrew G.,Knight, David W.
, p. 161 - 168 (2007/10/02)
Model studies have shown that the enolate Claisen rearrangement, a modification (developed by R.E.Ireland et al.) of the original Claisen rearrangement, can successfully be applied to the elaboration of medium-sized and large carbocycles from O-silyl enolates of suitable unsaturated macrolides (Scheme).The rearrangements are largely non-stereoselective, a fact which can be rationalised in terms of the intermediacy of both chair- and boat-like transition states and possibly because, in some cases, both the (E)- and (Z)-enolate of the macrolides are involved.
