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- Title
Asymmetric α-Hydroxylation of Tetralone-Derived β-Ketoesters by Using a Guanidine-Urea Bifunctional Organocatalyst in the Presence of Cumene Hydroperoxide.
- Authors
Odagi, Minami; Furukori, Kota; Watanabe, Tatsuya; Nagasawa, Kazuo
- Abstract
Highly enantioselective catalytic oxidation of 1-tetralone-derived β-keto esters was achieved by using a guanidine-urea bifunctional organocatalyst in the presence of cumene hydroperoxide (CHP), a safe, commercially available oxidant. The α-hydroxylation products were obtained in 99 % yield with up to 95 % enantiomeric excess ( ee). The present oxidation was successfully applied to synthesize a key intermediate of the anti-cancer agent daunorubicin ( 2).
- Subjects
HYDROXYLATION; TETRALONES; ESTERS analysis; GUANIDINE derivatives; ENANTIOSELECTIVE catalysis
- Publication
Chemistry - A European Journal, 2013, Vol 19, Issue 49, p16740
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201303006