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Synthetic routes to 1,4‐difunctionalized cycloheptenes
Author(s) -
Maier Martin E.,
Langenbacher Diane,
Rebien Frank
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199510258
Subject(s) - chemistry , cyclopentene , ketene , cycloheptene , yield (engineering) , ruthenium , bicyclic molecule , salt metathesis reaction , cycloaddition , catalysis , combinatorial chemistry , fragmentation (computing) , metathesis , medicinal chemistry , organic chemistry , materials science , polymer , computer science , metallurgy , polymerization , operating system
Two routes to 1,4‐difunctionalized cycloheptenes are described. The first one is based on a fluoride‐induced fragmentation reaction of the bicyclic [3.2.0]heptanesilyl monosulfate 10. This compound in turn was prepared by a ketene‐cyclopentene cycloaddition route. An alternative strategy took advantage of a ring‐closing metathesis (RCM) reaction of the diolefin 18 with the ruthenium catalyst 21. This reaction proved to be reliable even on a larger scale and allowed the isolation of the cycloheptene 19a in reasonably good yield.