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A new reagent system for installation of an aryl group onto the monoacetate of 4-cyclopentene-1,3-diol

✍ Scribed by Takayuki Ainai; Michiko Ito; Yuichi Kobayashi

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
173 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Among the three types of reagents from PhMgX (X=Br, Cl) and CuCN for phenylation of 4-cyclopentene-1,3-diol monoacetate, PhMgCl/CuCN (cat.) and Ph 2 Cu(CN)(MgCl) 2 in THF afforded the trans-1,4-isomer efficiently (82-87% yields, 91-93% regioselectivity). Similarly, o-and p-RC 6 H 4 MgCl (R=Me, OMe, CH 2 CH) in combination with CuCN furnished good to excellent reactivity and regioselectivity. As an application, a three-step synthesis of dihydromultifidene was accomplished successfully.

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