Low‐Temperature Photolysis of Peracetylated Dodecanoyl Peroxides of Tartaric Acid and  D ‐Gluconic Acid in the Solid State—A Diastereoselective Radical Coupling | Zendy

Lomölder Rainer | Zendy; Schäfer Hans J. | Zendy

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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.

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