期刊
CHINESE JOURNAL OF CHEMISTRY
卷 36, 期 12, 页码 1209-1212出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201800461
关键词
allylic alcohol; cyclic iodine reagents; quaternary all-carbon center; photoredox catalysis; alkyl boronate
资金
- National Natural Science Foundation of China [21472230, 21622207, 91753126]
- National Basic Research Program of China [2014CB910304]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20020200]
All-carbon quaternary centers are prevalent in bioactive small molecules. However, their efficient construction remains a formidable synthetic challenge. Here we report cyclic iodine(III) reagents enable the synthesis of cyclopentanones, cyclohexanones, and dihydrofuranones bearing alpha-quaternary centers by photoredox catalysis. The reaction proceeds by the formation of the novel cyclic iodine(III) reagent-allylic alcohol complex, which enables the first alkyl boronate addition and semi-pinacol rearrangement of allylic alcohols with dual alcohol and olefin activation. The reaction is suitable for gram scale synthesis and is transformable to alcohols, olefins, oximes, and lactones with an alpha-quaternary center in one step.
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