A supramolecular "ship in bottle" strategy for enantiomeric selectivity in geminate radical pair recombination.
[reaction: see text] Reactions in which zeolites are modified with chiral inductors to serve as media for chiral induction are often limited by the propensity of both substrate and inductor to occupy the same supercage. Herein, we report a "ship in bottle" strategy utilizing the thermal decomposition of dioxetanes obtained from oxazolidinone-substituted enecarbamates for the enantioselective generation of methyl desoxybenzoin (MDB). Photoexcitation of the supramolecular geminate molecular pair results in enrichment of the opposite enantiomer of MDB.
Poon
Thomas
T
Department of Chemistry, Columbia University, 3000 Broadway, Mail Code 3119, New York, New York 10027, USA.
Turro
Nicholas J
NJ
Chapman
Jessica
J
Lakshminarasimhan
P
P
Lei
Xuegong
X
Adam
Waldemar
W
Bosio
Sara G
SG