An efficient synthesis of brominated 4-alkyl-2(5H)-furanones
β Scribed by George Iskander; Ruonan Zhang; Daniel Shiu-Hin Chan; David StC Black; Mahiuddin Alamgir; Naresh Kumar
- Book ID
- 108285593
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 458 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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## Abstract Highly optically active 4βsubstitutedβ2(5__H__)βfuranones 6aβ6j were obtained in good yields with __de__β©Ύ98% by the tandem Michael addition/elimination reaction of chiral 3βbromoβ2(5__H__)βfuranone (4a), which was conveniently prepared starting from 2βfuraldehyde under mild conditions.
Easily available 3,4-dibromo-2(5H)-furanone undergoes a regioselective cross-coupling reaction with alkylboronic acids in the presence of catalytic amounts of PdCl2(MeCN)2 and AsPh3 and a large molar excess of Ag2O to provide the corresponding 4-alkyl-3-bromo-2(5H)-furanones in satisfactory yields.
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