Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 13, Pages 8660-8671Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00445
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Funding
- Swedish Research Council Formas [2019-00699]
- Operational Programme Research, Development and Education (Project Improvement of internationalization in the field of research and development) at Charles University [CZ.02.2.69/0.0/0.0/17_050/0008466]
- Formas [2019-00699] Funding Source: Formas
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This study successfully synthesized compounds with a specific structure using a special reaction method, providing a promising synthetic building block for further synthetic applications.
This study explores the synthesis of cyclic cis-vicinal phenyl ethylenes from oxotriphenylhexanoates. The reaction is a BBr3-promoted cyclization of 1,6-ketoesters (1) to five-membered diketo compounds (2). The synthesis is interesting as it constitutes one of the few examples of modular stereoselective synthesis of structures with a cis-oriented vicinal diphenylethylene. The core structure of 2 can be smoothly derivatized, which makes it a promising synthetic building block for further stereoselective synthetic applications.
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