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Chirality Solely Due to the Presence of an Excited State
Author(s) -
Meijer E. W.,
Wynberg Hans
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198809751
Subject(s) - racemization , excited state , chirality (physics) , molecule , photochemistry , chemistry , chemical physics , atomic physics , stereochemistry , physics , organic chemistry , quantum mechanics , symmetry breaking , chiral symmetry breaking , nambu–jona lasinio model
meso ‐Diketones in which only one carbonyl group is electronically excited must be chiral. A strategy for the synthesis of the first molecule of this kind is based on this concept. Starting from the optically active dioxetane 1 ( ee ca. 69%) the excited adamantanedione 2 was obtained, whose optical activity, however, could not be ascertained experimentally since the close spatial proximity of the carbonyl groups enables rapid racemization in the excited state.