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TFA-mediated intramolecular Friedel–Crafts reaction. An efficient metal and halogen free route to stereoselective synthesis of benzocycles

✍ Scribed by Shengming Ma; Junliang Zhang

Book ID: 104205610
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 372 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)01026-3

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✦ Synopsis

6-Acetoxy-4-alkenyl arenes undergo regio-and stereoselective intramolecular Friedel -Crafts reaction affording benzocycles in moderate to excellent yields in TFA/HOAc (3:1). It was observed that introduction of alkyls or phenyl group to the allylic acetate moiety facilitates the cyclization reaction. The optically active tricyclic (4bR,8aS)-4b,7,8,8a,9,10-hexahydrophenanthrene skeleton could also be easily obtained in excellent yields.

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