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Stereoselectivity of the Hydrogen‐Atom Transfer in Benzophenone–Tyrosine Dyads: An Intramolecular Kinetic Solvent Effect
Author(s) -
Hörner Gerald,
Hug Gordon L.,
Lewandowska Anna,
Kazmierczak Franciszek,
Marciniak Bronislaw
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802674
Subject(s) - chemistry , intramolecular force , hydrogen atom , diastereomer , solvent , ketone , photochemistry , hydrogen bond , benzophenone , solvent effects , stereoselectivity , hydrogen , hydrogen atom abstraction , stereochemistry , molecule , organic chemistry , catalysis , alkyl
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).