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Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition

Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan
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Academic Editor: Norbert Haider
Molbank 2016, 2016(4), M908; https://doi.org/10.3390/M908
Received: 31 July 2016 / Revised: 19 September 2016 / Accepted: 19 September 2016 / Published: 22 September 2016
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed Ti-direct aldol addition and (ii) an acid-induced characteristic cyclo-condensation, leading to 2(5H)-furanones. Suzuki-Miyaura cross-coupling of 5-(4-bromophenyl)-furan-2(5H)-ones, 5-(4-tosyloxyphenyl)-3,4-dimethylfuran-2(5H)-ones and a furan derivative successfully afforded the corresponding products with the 2(5H)-furanone skeleton. View Full-Text
Keywords: Cross-aldol reaction; titanium chloride; furanone; furanone annulation; Ti-mediated reaction; 1,1-dimethoxyacetone; bromophenyl ketone; tosyloxy ketone; cross-coupling partner; Suzuki-Miyaura cross-coupling Cross-aldol reaction; titanium chloride; furanone; furanone annulation; Ti-mediated reaction; 1,1-dimethoxyacetone; bromophenyl ketone; tosyloxy ketone; cross-coupling partner; Suzuki-Miyaura cross-coupling
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MDPI and ACS Style

Ban, Y.; Ashida, Y.; Nakatsuji, H.; Tanabe, Y. Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition. Molbank 2016, 2016, M908.

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