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Synfacts 2005(2): 0267-0267
DOI: 10.1055/s-2005-916088
DOI: 10.1055/s-2005-916088
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York05SF
A Selenium Tether for the Solid-Phase Preparation of Isoxazolines
W.-M. Xu, Y.-G. Wang, M.-Z. Miao, X. Huang*
Zhejiang University, P. R. of China
Further Information
Publication History
Publication Date:
25 October 2005 (online)
Significance
A novel cleavage method for polystyrene-supported selenium and the solid-phase preparation of 3,5-disubstituted isoxazolines are described. Polymer-supported isoxazolines were prepared from polystyrene-supported selenyl bromide in three steps. Cleavage of the resulting polymer-supported isoxazolines was performed with CH3I/NaI in DMF (80 °C, 24 h) to afford the corresponding 3-substituted 5-(iodomethyl)isoxazolines in 71-87% yields (7 examples, R = Ph, 4-substituted phenyl, ethoxycarbonyl). The polystyrene-supported methyl selenide was recovered and reused four times without loss of purity of the products.