期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 18, 期 15, 页码 2817-2822出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00468e
关键词
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资金
- European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013)/ERC grant [277588]
- Greek General Secretariat of Research and Technology [KA: 4143]
- Alexander S. Onassis Public Benefit Foundation [G ZM 063-1/2016-2017]
A new methodology is described herein which converts simple and readily accesible furan substrates into complex enantio-enriched carbocyclic skeletons through the implementation of a simple one-pot procedure. Singlet oxygen furan photoxygenation affords an enedione which then participates in an organocatalysed double-Michael reaction with an enal to furnish a cyclopentanone structure with up to four new contiguous stereogenic centres. The enantioselectivity and diastereoselectivity of this process are both excellent. If desired, further aldol-annulation steps can be appended to the cascade reaction sequence to afford key enantiopure hydrindane motifs.
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