Solid-State Structural Investigation of an Organolithium (−)-Sparteine Complex:η3-N-Boc-N-(p-methoxyphenyl)-3-phenylallyllithium⋅(−)-Sparteine

Abstract

A η³ monomeric alkyllithium⋅(-)-sparteine complex has been isolated and characterized in the solid state (see picture). Determination of the absolute configuration of this key intermediate in asymmetric metalation/substitution sequences of N-tert-butoxycarbonyl-N-(p-methoxyphenyl)cinnamylamine allows definitive assignment of the stereochemical course of its electrophile-dependent substitution reactions.