Tetrahedron letters

Synthesis of Z-allylic acetates via fragmentation of cyclic homoallylic alcohols

P Ramaiah, AS Rao

Index: Ramaiah, P.; Rao, A. S. Tetrahedron Letters, 1988 , vol. 29, # 17 p. 2119 - 2120

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Citation Number: 3

Abstract

: Compounds and were prepared in 80% yields by reducing the corresponding ketones 5 and 6 with NaBH 4 in methanol at 25°C. Compounds , and were prepared in 70%, 60% and 65% yields by reacting ketone 5 with phenyl-magnesium bromide, 4-methoxy phenylmagnesium bromide and methylmagnesium iodide respectively. They were purified by column chromatography over Al 2 O 3 . ... Compound showed bp 120°C/5 mm; reported 8a bp 105°C/2mm. The 1 ...