期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 45, 页码 19354-19359出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c09638
关键词
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资金
- National Key R&D Program of China [2016YFA0202900]
- NSFC [21532010, 21772219, 21821002]
- Science and Technology Commission of Shanghai Municipality [18QA1404900]
- Chinese Academy of Sciences [XDB20000000, QYZDY-SSW-SLH012]
- Youth Innovation Promotion Association of CAS [2017302]
- Tencent Foundation through the XPLORER PRIZE
Spirocyclic hexadienones with multiple stereogenic centers are frequently found in natural products but remain challenging targets to synthesize. Herein, we report the enantioselective desymmetrization of bisphenol derivatives via Ir-catalyzed allylic dearomatization reactions, affording spirocyclic hexadienone derivatives with up to three contiguous stereogenic centers in good yields (up to 90%) and excellent enantioselectivity (up to 99% ee). The high efficiency of this reaction is exemplified by the short reaction time (30 min), low catalyst loading (down to 0.2 mol %), and ability to perform the reaction on a gram-scale. The total syntheses of (+)-tatanan B and (+)-tatanan C were also realized using this Ir-catalyzed allylic dearomatization reaction as a key step.
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