ChemInform Abstract: (-)-Sparteine-Mediated Asymmetric Cyclocarbolithiation of Alkenes Combined with a Stereospecific retro-[1,4]-Brook Rearrangement.
Abstract
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ChemInform Abstract
A novel stereoselective cyclocarbolithiation—retro-[1,4]-Brook rearrangement reaction cascade of silyloxyarylhexenyl carbamates (I) is described. The internal [O→C] silyl transfer proceeds with retention of the configuration at the benzylic position to furnish optically pure (α-silylbenzyl)cyclopentane derivatives (II), and, moreover, it suppresses the undesired 1,3-cycloelimination to bicyclic compounds (III).
