1269416-96-7Relevant articles and documents
Iterative stereospecific reagent-controlled homologation using a functionalized α-chloroalkyllithium: Synthesis of cyclic targets related to epibatidine
Emerson, Christopher R.,Zakharov, Lev N.,Blakemore, Paul R.
supporting information; experimental part, p. 1318 - 1321 (2011/04/26)
Enantioenriched 1-chloro-2-(1,3-dioxolan-2-yl)ethyllithium was generated by PhLi initiated sulfoxide-ligand exchange and deployed in situ for sequential double stereospecific reagent-controlled homologation (StReCH) of B-(2-chloro-pyrid-5-yl) pinacol boronate. This process afforded highly functionalized contiguous stereodiad motifs (typically, % ee ≥ 98%, dr ≥ 85:15) amenable to subsequent annulative transformations as demonstrated by the concise synthesis (5-7 steps) of cyclic adducts related to the analgesic alkaloid epibatidine.