Realization of Anti-SN2' Selective Allylation of 4-Cyclopentene-1,3-diol Monoester with Aryl- and Alkenyl-Zinc Reagents

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• 作者：Kenya Nakata ; Yohei Kiyotsuka ; Tomoya Kitazume ; Yuichi Kobayashi
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：April 3, 2008
• 年：2008
• 卷：10
• 期：7
• 页码：1345 - 1348
• 全文大小：74K
• 年卷期：v.10,no.7(April 3, 2008)
• ISSN：1523-7052

文摘

Anti-S_N2' mode of allylation of the monoester of 4-cyclopentene-1,3-diol with aryl and alkenyl anions was achieved, for the first time, with theMeOCH₂CO₂- group as a leaving group to which R-ZnBr and CuCl (as a catalyst) were best fitted. The aryl groups successfully installed werePh, o- and p-MeC₆H₄, o-MOMOC₆H₄, o-MeOC₆H₄, and p-F-C₆H₄, while cis and trans alkenyl groups were attached with retention of the olefinicstereochemistries.