A three-component approach to isoquinoline derivatives by cycloaddition/Heck reaction sequence |
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Authors: | Masato Oikawa Yoshiyuki Takeda Daisuke Hashizume Makoto Sasaki |
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Institution: | a Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Tsutsumidori-Amamiya, Aoba-ku, Sendai 981-8555, Japan b Molecular Characterization Team, Advanced Development and Supporting Center, RIKEN, Hirosawa 2-1, Wako, Saitama 351-0198, Japan |
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Abstract: | Here, we report a three-component coupling reaction approach between an aldehyde, an allyloxyamine, and a maleimide toward isoquinoline derivatives. At first, an oxime O-allylic ether, prepared by dehydrative condensation of the aldehyde and the allyloxyamine, was reacted with the maleimide in the presence of a Pd2+ species. The cycloadduct obtained was then subjected to the Heck cyclization employing a Pd0 species to give thermodynamically stable diastereomer of isoquinoline derivatives selectively in 25-78% yields. |
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