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Stereoselective Double Functionalization of Iron-Carbonyl Complexes of 5,6,7,8-Tetramethylidenebicyclo[2.2.2]oct-2-ene. Crystal Structure and Absolute Configuration of (–)-trans-μ-[(2S,5R,7S)-C,5,6,C-η:C,7,8,C-η-(6,7,8-trimethylidene-5-((Z)-2-oxopropylidene)-2-bicyclo[2.2.2]octyl acetate)]-bis(tricarbonyliron)

✍ Scribed by Enrico Tagliaferri; Philippe Campiche; Raymond Roulet; Raphy Gabioud; Pierre Vogel; Gervais Chapuis

Publisher
John Wiley and Sons
Year
1985
Tongue
German
Weight
559 KB
Volume
68
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The Friedel‐Crafts monoacylation of trans‐η‐[(1__RS__,2__RS__,4__SR__,5__SR__,6__RS__,7__SR__,8__SR__)‐C,5,6,C‐η:C,7,8,C‐η‐(5,6,7,8‐tetramethylidene‐2‐bicyclo[2.2.2]octyl acetate)]‐bis(tricarbonyliron) ((±)‐5) is highly stereoselective and yields trans‐η‐[(1__RS__,2__RS__,4__RS__,5__SR__,6__RS__,7__RS__,8__SR__)‐C,6‐η,oxo‐σ:C,7,8,C‐η‐(6,7,8‐trimethylidene‐5‐((Z)‐2‐oxopropylidene)‐2‐bicyclo[2.2.2]octyl acetate)]‐bis(tricarbonyliron) ((±)‐8) which equilibrates with the trans‐η‐[(1__RS__,2__RS__,4__RS__,5__SR__,6__RS__,7__RS__,8__SR__)‐C,5,6,C‐η:C,7,8,C‐η‐(6,7,8‐trimethylidene‐5‐((Z)‐2‐oxopropylidene)‐2‐bicyclo[2.2.2]octyl acetate)]‐bis(tricarbonyliron) ((±)‐9) on heating. Optically pure (–)‐9 has been prepared from the corresponding optically pure alcohol (+)‐4. The structure and absolute configuration of (–)‐9 was established by single‐crystal X‐ray diffraction.

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