Iron??Mediated and??Catalyzed Metalative Cyclization of Electron??Withdrawing??Group??Substituted Alkynes and Alkenes with Grignard Reagents

…, S Sujaku, N Hirone, K Nakano, J Imoto…

Index: Hata, Takeshi; Sujaku, Shiro; Hirone, Naoki; Nakano, Kirihiro; Imoto, Junsuke; Imade, Haduki; Urabe, Hirokazu Chemistry - A European Journal, 2011 , vol. 17, # 51 p. 14593 - 14602

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Citation Number: 11

Abstract

Abstract Treatment of ethyl (E)-5, 5-bis [(benzyloxy) methyl]-8-(N, N-diethylcarbamoyl)-2- octen-7-ynoate with an iron reagent generated from FeCl 2 and tBuMgCl in a ratio of 1: 4 (abbreviated as FeCl 2/4 tBuMgCl) afforded ethyl [4, 4-bis [(benzyloxy) methyl]-2-[(E)-(N, N- diethylcarbamoyl) methylene] cyclopent-1-yl] acetate in good yield. Deuteriolysis of an identical reaction mixture afforded the bis-deuterated product ethyl [4, 4-bis [(benzyloxy) ...