Lithium aluminum hydride reduction of allylic substrates. Notable leaving group effects on the product regiochemistry

T Hirabe, M Nojima, S Kusabayashi

Index: Hirabe, Tomoatsu; Nojima, Masatomo; Kusabayashi, Shigekazu Journal of Organic Chemistry, 1984 , vol. 49, # 21 p. 4084 - 4086

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Citation Number: 16

Abstract

" The reaction with 5 molar equiv of LAH in ether at 20" C for 1 h. bThe reaction with 5 molar equiv of AlH, in tetrahydrofuran at 20" C for 1 h. cThe isolated yield. dThe phosphonium salt was generated in situ by the reaction of the corresponding ylide with methyl iodide. The E/Z ratio determined by'H NMR spectroscopy was about 2: 3. this interesting transformation, 3c we performed the reaction of a series of phosphonium salta with LAH (Table 11). The data ...