title: Quantum-mechanical study of 10-R-9-borabicyclo[3.3.2]decane alkene hydroboration.
abstract: Density functional theory and correlated ab initio quantum mechanical methods were used to locate and analyze alkene hydroboration transition structures for 10-R-9-borabicyclo[3.3.2]decane reagents. Transition-state ensembles quantitatively modeled enantioselectivity for hydroboration of cis-, trans-, and gem-disubstituted alkenes in excellent agreement with experiment. The 10-R group and borabicyclo[3.3.2]decane ring conformation effects were analyzed to understand the origin of asymmetric selectivity.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA. daniel@scripps.edu
authors.forename: Daniel H
authors.initials: DH
authors.lastname: Ess
authors.forename: Jeremy
authors.initials: J
authors.lastname: Kister
authors.forename: Ming
authors.initials: M
authors.lastname: Chen
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D003198:Computer Simulation; D008956:Models, Chemical; D011789:Quantum Theory
chemical_list: C546486:10-R-9-borabicyclo(3.3.2)decane; D000475:Alkenes; D001643:Bridged Bicyclo Compounds