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Synthetic routes to 1,4-difunctionalized cycloheptenes

✍ Scribed by Maier, Martin E. ;Langenbacher, Diane ;Rebien, Frank

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
712 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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.

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