title: Highly Stereoselective Synthesis of Terminal Chloro-Substituted Propargylamines and Further Functionalization.
abstract: The highly stereoselective addition of lithiated chloroacetylene, derived in situ from cis-1,2-dichloroethene and methyl lithium, to Ellman chiral N-tert-butanesulfinyl imines is reported. The reaction proceeds in high yield (up to 98%) and with excellent diastereoselectivity (up to >20:1) for a variety of aryl, heteroaromatic, alkyl, and α,β-unsaturated imine substrates. Transformations of the terminal chloro-substituted propargylamine products are described in which lithium-halogen exchange yields nucleophilic acetylides that can be quenched to yield terminal alkynes or intercepted by carbon electrophiles.
authors.affiliation: Department of Chemistry, Berry College , Mount Berry, Georgia 30149, United States.
authors.forename: Savannah
authors.initials: S
authors.lastname: Jordan
authors.affiliation: Department of Chemistry, Berry College , Mount Berry, Georgia 30149, United States.
authors.forename: Samuel A
authors.initials: SA
authors.lastname: Starks
authors.affiliation: Department of Chemistry, Berry College , Mount Berry, Georgia 30149, United States.
authors.forename: Michael F
authors.initials: MF
authors.lastname: Whatley
authors.affiliation: Department of Chemistry, Berry College , Mount Berry, Georgia 30149, United States.
authors.forename: Mark
authors.initials: M
authors.lastname: Turlington