✦ LIBER ✦

A new and unusually flexible scheme for annulatton to form fused cyclohexenone units

✍ Scribed by E.J. Corey; Dale L. Boger

Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 350 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85680-x

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✦ Synopsis

We have recently described two different types of annulation methods leading to fused and Spiro ring systems, one based on benzothiazoles as carbonyl equivalents' and the other on the use of pyridinium chlorochromate as a reagent for oxidative cation-olefin cyclization.

2 In continuation of our research on new annulation techniques we next turned tc the exploitation of certain of the recently reported reactions of organometallic derivatives of N, N-dimethylhydrazones, 3.4 available by metallation (HuLi or lithium diisopropylamide) and subsequent reaction with cuprous iodide. Such Gilman reagents can be used effectively as enolate equivalents for conjugate addition to cu,P-unsaturated esters. 5 Thus ethyl l-cyclohexene-l-24. F J. Corey andS. Knapp, TetrahedronLett., 3667 (1976).

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