This document details the Sharpless epoxidation, a Nobel Prize-winning reaction for the enantioselective synthesis of 2,3-epoxy alcohols from allylic alcohols. Key aspects include:
Reagents: Titanium tetraisopropoxide [Ti(OiPr)₄], diethyl tartrate (DET), and tert-butyl hydroperoxide (TBHP).
Mechanism:
Coordination of the allylic alcohol’s OH group to titanium.
Enantioselective epoxidation controlled by chiral tartrate ligands [(+)-DET or (−)-DET].
Applications:
Synthesis of chiral epoxy alcohols, precursors to diols, amino alcohols, and complex natural products.
Widely used in pharmaceutical synthesis (e.g., beta-blockers, antifungals).
Stereochemistry: Predictable enantioselectivity (up to >90% ee) based on the tartrate isomer used.
Find what you need faster with our free app!
In case, Feaures are not working on this website, please update your browser or use another browser. View Supported Browser List. Further if you think this is an error, please feel free to contact us at [email protected] or you may also Chat with us.
