期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 31, 页码 9762-9769出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201402684
关键词
asymmetric catalysis; cinchona alkaloid; isothiourea; Michael addition; organocatalysis; oxygen heterocycles; stereodivergent
资金
- Royal Society for a University Research Fellowship
- European Research Council under the European Union, ERC [279850]
- EPSRC (DTA studentship)
A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available (S)-(-)-tetramisole hydrochloride gives products with high syn diastereoselectivity in excellent enantioselectivity (up to 99:1 d.r.(syn/anti), 99% ee(syn)), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti-diastereoisomers as the major product (up to 10:90 d.r.(syn/anti), 99% ee(anti)).
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