Related Experiment Video
Updated: Jul 12, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Direct Stereospecific Deoxyamination of Alcohols Enabled by Li-Mediated SuFEx
Amaechi S Odoh1, Giovani Gutierrez1, Austin G Seilkop1
1Clemson University, South Palmetto Boulevard, Clemson, South Carolina 29634, United States.
Abstract:
Optically active nitrogen-bearing molecules are central to drug discovery, which has driven the development of efficient, stereocontrolled C(sp3)-N bond-forming methods. Herein we report a SuFEx-enabled platform that directly couples diverse alcohols and free N-nucleophiles via deoxygenative C(sp3)-N(sp3/sp2) bond formation with high stereospecificity without elimination. Using an inexpensive lithium triflate salt to suppress competitive deoxyfluorination, this method enables facile deoxyamination with broad substrate scope, N-heterocycle synthesis, late-stage functionalization, and stereodivergent synthesis of pharmaceuticals.
Related Concept Videos
Conversion of Alcohols to Alkyl Halides
Acid Halides to Esters: Alcoholysis
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Acid-Catalyzed Dehydration of Alcohols to Alkenes
Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
