title: Asymmetric lithiation-substitution of amines involving rearrangement of borates.
abstract: Asymmetric lithiation of substituted benzylamines, N-Boc-pyrrolidine, or N-Boc-indoline using Beak's methodology was followed by electrophilic quench with trialkylboranes. The resulting borate intermediates rearrange with concomitant C-N bond breakage to give, after oxidation, chiral secondary alcohols with high enantioselectivity.
authors: Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK. i.coldham@sheffield.ac.uk
authors: Iain
authors: I
authors: Coldham
authors: Jignesh J
authors: JJ
authors: Patel
authors: Sophie
authors: S
authors: Raimbault
authors: David T E
authors: DT
authors: Whittaker
authors: Harry
authors: H
authors: Adams
authors: Guang Y
authors: GY
authors: Fang
authors: Varinder K
authors: VK
authors: Aggarwal
mesh_terms: D000588:Amines / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry; D018360:Crystallography, X-Ray; D008094:Lithium / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013034:Sparteine / Q000737:chemistry
chemical_list: D000588:Amines; D001881:Borates; D002219:Carbamates; D009942:Organometallic Compounds; D013034:Sparteine; D008094:Lithium