Stereoselectivity of the hydrogen-atom transfer in benzophenone-tyrosine dyads: an intramolecular kinetic solvent effect.
To be or not to be solvated is the decisive parameter that controls the photoinduced hydrogen-atom transfer in diastereomeric ketone/phenol dyads. A kinetic solvent effect that refers to hydrogen bonding between the phenol and the solvent is suggested to be the main source of the stereoselective discrimination in the hydrogen transfer (see figure).
Hörner
Gerald
G
Faculty of Chemistry, Adam Mickiewicz University Poznan, Grunwaldzka 6, 60780 Poznan, Poland. hoerner@amu.edu.pl
Hug
Gordon L
GL
Lewandowska
Anna
A
Kazmierczak
Franciszek
F
Marciniak
Bronislaw
B
D001577:Benzophenones / Q000737:chemistry*; D006860:Hydrogen Bonding; D007659:Ketones; D007700:Kinetics; D015394:Molecular Structure; D010777:Photochemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D014443:Tyrosine / Q000737:chemistry*
D001577:Benzophenones; D007659:Ketones; D012997:Solvents; D014443:Tyrosine; C047723:benzophenone