Aryl Acetate Phase Transfer Catalysis: Method and Computation Studies

• Main Author: Binkley, Meisha A.
• Format: Others
• Published: BYU ScholarsArchive 2011
• Subjects: Phase Transfer Catalysis; cinchona catalyst; asymmetric alkylation; transition state determination; computational chemistry; Biochemistry; Chemistry
• Online Access: https://scholarsarchive.byu.edu/etd/2680; https://scholarsarchive.byu.edu/cgi/viewcontent.cgi?article=3679&context=etd

Brief explanation and history of cinchona based Phase Transfer Catalysis (PTC). Studied aryl acetates in PTC, encompassing napthoyl, 6-methoxy napthoyl, phenyl and protected 4-hydroxy phenyl acetates. Investigated means of controlling the selectivity of the PTC reaction by changing the electrophile size, the ether side group size or by addition of inorganic salts. Found that either small or aromatic electophiles increased enantioselectivity more than aliphatic electrophiles, and that increasing the size of ether protecting group also increased selectivity. Positive effects of salt addition included either decreasing reaction time or increasing enantiomeric excess. Applied findings towards the synthesis of S-equol. Computational experiments working towards deducing the transition state between PTC and aryl acetate substrates.