A new reagent system for installation of an aryl group onto the monoacetate of 4-cyclopentene-1,3-diol
作者:Takayuki Ainai、Michiko Ito、Yuichi Kobayashi
DOI:10.1016/s0040-4039(03)00777-9
日期:2003.5
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 Ph2Cu(CN)(MgCl)(2) in THF afforded the trans- 1,4-isomer efficiently (82-87% yields, 91-93% regioselectivity). Similarly, o- and p-RC6H4MgCl (R = Me, OMe, CH2=CH) in combination with CuCN furnished good to excellent reactivity and regioselectivity. As an application, a three-step synthesis of dihydromultifidene was accomplished successfully. (C) 2003 Elsevier Science Ltd. All rights reserved.