Quantum-mechanical study of 10-R-9-borabicyclo[3.3.2]decane alkene hydroboration.
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.
Ess
Daniel H
DH
Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA. daniel@scripps.edu
Kister
Jeremy
J
Chen
Ming
M
Roush
William R
WR
D000475:Alkenes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D003198:Computer Simulation; D008956:Models, Chemical; D011789:Quantum Theory
C546486:10-R-9-borabicyclo(3.3.2)decane; D000475:Alkenes; D001643:Bridged Bicyclo Compounds