title: Catalytic 1,3-difunctionalisation of organic backbones through a highly stereoselective, one-pot, boron conjugate-addition/reduction/oxidation process.
abstract: A simple one-pot, three-step synthetic route to chiral 1,3-amino alcohols and 1,3-diols has been established. Considering the overall stereocontrol of the synthetic protocol, the first and key step is an enantioselective β-boration of α,β-unsaturated imines and ketones, respectively. The enantioselectivity provided by the Cu(I) catalyst modified with Josiphos- and Mandyphos-type ligands has been examined. The oxidative substitution of the boryl unit with a hydroxyl group proceeds with complete retention of configuration at the C(β)-atom. In parallel, the stoichiometric reduction of the imino or carbonyl group provides a second stereogenic centre. Depending on the nature of the reducing reagent, exceptionally high diastereoselectivity is achieved, especially for syn-1,3-amino alcohols and 1,3-diols.
authors.affiliation: Departament Química Física i Inorgànica, University Rovira i Virgili, C/Marcel.lí Domingo s/n, 43007 Tarragona, Spain.
authors.forename: Cristina
authors.initials: C
authors.lastname: Solé
authors.forename: Amolak
authors.initials: A
authors.lastname: Tatla
authors.forename: Jose A
authors.initials: JA
authors.lastname: Mata
authors.forename: Andrew
authors.initials: A
authors.lastname: Whiting
authors.forename: Henrik
authors.initials: H
authors.lastname: Gulyás
authors.forename: Elena
authors.initials: E
authors.lastname: Fernández