期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 24, 期 13, 页码 3209-3217出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201704624
关键词
chemoenzymatic; heterocycles; lipase; sigmatropic; transition metal catalysis
资金
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft [DE 1599/4-1]
- Dr.-Otto-Rohm-Gedachtnisstiftung
A novel chemoenzymatic synthetic cascade enables the preparation of densely decorated tetrahydrofuran building blocks. Here, the lipase-catalyzed desymmetrization of 3-alkoxyglutarates renders highly enantioenriched carboxylic acid intermediates, whose subsequent activation and oxonium ylide rearrangement by means of rhodium or copper complexes furnishes functionalized O-heterocycles with excellent diastereoselectivity. The two-step protocol offers a streamlined and flexible synthesis of tetrahydrofuranones bearing different benzylic, allylic or allenylic side chains with full control over multiple stereogenic centers.
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