title: Enantioselective syntheses of (+)-sertraline and (+)-indatraline using lithiation/borylation-protodeboronation methodology.
abstract: The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCl, H(2)O), or a solvent switch to CHCl(3), to achieve high yields and high selectivities.
authors: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors: Stefan
authors: S
authors: Roesner
authors: Javier Mansilla
authors: JM
authors: Casatejada
authors: Tim G
authors: TG
authors: Elford
authors: Ravindra P
authors: RP
authors: Sonawane
authors: Varinder K
authors: VK
authors: Aggarwal
mesh_terms: D001895:Boron / Q000737:chemistry*; D007189:Indans / Q000138:chemical synthesis*; D008094:Lithium / Q000737:chemistry*; D008744:Methylamines / Q000138:chemical synthesis*; D015394:Molecular Structure; D011522:Protons; D020280:Sertraline / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D007189:Indans; D008744:Methylamines; D011522:Protons; C418119:indatraline; D008094:Lithium; D001895:Boron; D020280:Sertraline