title: Kinetic resolution of racemic lactones by conjugate additions of allylic organolithium species: direct formation of three contiguous centers with high diastereo- and enantioselectivities.
abstract: [reaction: see text] Kinetic resolution of racemic alpha,beta-unsaturated lactones by the organolithium species produced from asymmetric lithiation of N-Boc-N-(p-methoxyphenyl)cinnamylamine provides conjugate addition products with three contiguous stereogenic centers in yields of 62-77% with diastereomeric ratios from 75:25 to >99:1 and enantiomeric ratios for the major diastereomers from 94:6 to 98:2.
authors.affiliation: Department of Chemistry, University of Illinois at Urbana-Champaign, 61801, USA.
authors.forename: Sung H
authors.initials: SH
authors.lastname: Lim
authors.forename: Peter
authors.initials: P
authors.lastname: Beak
mesh_terms: D018360:Crystallography, X-Ray; D007700:Kinetics; D007783:Lactones / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D018020:Lithium Compounds; D009942:Organometallic Compounds