Asymmetric α‐Hydroxylation of Tetralone‐Derived β‐Ketoesters by Using a Guanidine–Urea Bifunctional Organocatalyst in the Presence of Cumene Hydroperoxide | Zendy

Odagi Minami | Zendy; Furukori Kota | Zendy; Watanabe Tatsuya | Zendy; Nagasawa Kazuo | Zendy

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Asymmetric α‐Hydroxylation of Tetralone‐Derived β‐Ketoesters by Using a Guanidine–Urea Bifunctional Organocatalyst in the Presence of Cumene Hydroperoxide

Author(s) -

Odagi Minami,

Furukori Kota,

Watanabe Tatsuya,

Nagasawa Kazuo

Publication year - 2013

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201303006

Subject(s) - chemistry , guanidine , bifunctional , hydroxylation , cumene , cumene hydroperoxide , urea , organocatalysis , organic chemistry , catalysis , enantioselective synthesis , enzyme

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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