Titanium??Mediated Addition of Grignard Reagents to Acyl Cyanohydrins: Aminocyclopropane versus 1, 4??Diketone Formation

…, F Boeda, MSM Pearson??Long, P Bertus

Index: Setzer, Paul; Forcher, Gwenael; Boeda, Fabien; Pearson-Long, Morwenna S. M.; Bertus, Philippe European Journal of Organic Chemistry, 2014 , vol. 2014, # 1 p. 171 - 180

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Citation Number: 2

Abstract

Abstract The 1, 2-dianion reactivity of the reagent generated from EtMgBr and titanium isopropoxide was illustrated when N-acyl cyanohydrins were used as substrates (> 20 examples), giving both aminocyclopropane derivatives and 1, 4-dicarbonyl compounds. When the reaction was performed in diethyl ether, 5-hydroxy-1, 4-diketones were the main product. Under specific conditions (use of tetrahydrofuran and a bulky carboxylic moiety), ...