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Synfacts 2010(9): 1088-1088  
DOI: 10.1055/s-0030-1257979
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

SiO2-Mediated Allylic Rearrangement Under Microwave Irradiation

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
A. Serra-Muns, A. Guérinot, S. Reymond*, J. Cossy*
ESPCI ParisTech, France
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Publikationsdatum:
23. August 2010 (online)

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Significance

Efficient allylic rearrangement using a silica gel catalyst under microwave irradiation was described. Reactions of a variety of allylic ­acetates 1 (0.2-0.4 M) with silica gel (weight ratio substrate/silica gel = 1:4) were carried out in dichloromethane or 1,2-dichloroethane under ­microwave irradiation (15-30 min, 80 or 120 ˚C) to give the rearranged products 2. Propargylic allylic acetates 3 underwent the silica gel mediated rearrangement to give the corresponding 1,3-enynes 4.