Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 45, Pages 19354-19359Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c09638
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Funding
- 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
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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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