Asymmetric α‐Hydroxylation of Tetralone‐Derived β‐Ketoesters by Using a Guanidine–Urea Bifunctional Organocatalyst in the Presence of Cumene Hydroperoxide |
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| Authors: | Minami Odagi Kota Furukori Tatsuya Watanabe Prof. Dr. Kazuo Nagasawa |
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| Affiliation: | Department of Biotechnology and Life Science, Faculty of Engineering, Tokyo University of Agriculture and Technology, 2‐24‐16, Naka‐cho, Koganei, Tokyo 184‐8588 (Japan), Fax: (+81)?42‐388‐7295 |
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| 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 ). |
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| Keywords: | esters enantioselectivity hydroxylation organocatalysis oxidation synthetic methods |
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