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‐[(2 S ,5 R ,7 S )‐ 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) | Zendy

Tagliaferri Enrico | Zendy; Campiche Philippe | Zendy; Roulet Raymond | Zendy; Gabioud Raphy | Zendy; Vogel Pierre | Zendy; Chapuis Gervais | Zendy

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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‐[(2 S ,5 R ,7 S )‐ 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)

Author(s) -

Tagliaferri Enrico,

Campiche Philippe,

Roulet Raymond,

Gabioud Raphy,

Vogel Pierre,

Chapuis Gervais

Publication year - 1985

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19850680116

Subject(s) - chemistry , stereoselectivity , absolute configuration , crystal structure , stereochemistry , bicyclic molecule , ene reaction , surface modification , alcohol , medicinal chemistry , crystallography , catalysis , organic chemistry

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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