On the mechanism of base-induced rearrangements of epoxides to ketones: a formal synthesis of (S)-physoperuvine

The enantioselective α-deprotonation-rearrangement of trans- and cis-5-silyloxycycloheptene oxides (trans-8 and cis-8) using organolithiums in the presence of (-)-sparteine 16 or (-)-α-isosparteine 17 to give predominantly 4-silyloxycycloheptanone [(R)-9 (up to 87% ee), a known intermediate in the s...

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Bibliographic Details
Main Authors: Hodgson, D, Robinson, L, Jones, M
Format: Journal article
Language:English
Published: 1999