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Low‐Temperature Photolysis of Peracetylated Dodecanoyl Peroxides of Tartaric Acid and D ‐Gluconic Acid in the Solid State—A Diastereoselective Radical Coupling
Author(s) -
Lomölder Rainer,
Schäfer Hans J.
Publication year - 1987
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.198712531
Subject(s) - chemistry , steric effects , radical , photodissociation , solid state , isobutyraldehyde , tartaric acid , carboxylic acid , organic chemistry , polymer chemistry , catalysis , citric acid
The title reaction permits carboxylic acids of the chiral pool to be modified at the asymmetric center with retention of configuration . It is not only preparatively simple but also mechanistically interesting. By steric fixation of radicals in the solid state an otherwise unselective coupling becomes a diastereo‐selective one. The chemical yields are 40–60%, the diastereo‐selectivities 90–95% de.