title: Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency.
abstract: Sodium TMP-zincate, [(TMEDA)Na(TMP)((t)Bu)Zn((t)Bu)], can deproto-zincate N-Boc pyrrolidine at ambient temperature in hexane solution, whereas in toluene the captured α-carbanion of the heterocycle attacks the solvent setting off a cascade of reactions that ultimately produce a pyrrolidine-substituted enolate.
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK.
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Garden
authors.forename: Alan R
authors.initials: AR
authors.lastname: Kennedy
authors.forename: Robert E
authors.initials: RE
authors.lastname: Mulvey
authors.forename: Stuart D
authors.initials: SD
authors.lastname: Robertson
mesh_terms: D018360:Crystallography, X-Ray; D006586:Hexanes / Q000737:chemistry; D008968:Molecular Conformation; D011759:Pyrrolidines / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013696:Temperature; D015032:Zinc / Q000737:chemistry*
chemical_list: D006586:Hexanes; C531441:N-Boc-pyrrolidine; D011759:Pyrrolidines; D012997:Solvents; D015032:Zinc