Tetrahedron

Studies on organolithium-induced alkylative desymmetrisation of epoxides: synthesis of enantioenriched β-amino cycloheptenols from 6, 7-epoxy-8-azabicyclo [3.2. 1] …

DM Hodgson, E Paruch

Index: Hodgson, David M.; Paruch, Edyta Tetrahedron, 2004 , vol. 60, # 24 p. 5185 - 5199

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Citation Number: 14

Abstract

The synthesis and enantioselective α-deprotonation—double ring opening of 6, 7-epoxy-8- azabicyclo [3.2. 1] octanes using organolithiums in the presence of (−)-sparteine or (4S)-2, 2′-(1-ethylpropylidene) bis-4-(1-methylethyl)-4, 5-dihydrooxazole, giving amino cycloheptenols in up to 85% yield and 82% ee is described. The impact of different reaction variables on reaction profiles has been studied, including the nature of organolithium, ...