Construction of 1,3-Oxazolidines through a Three-Component [3+2] Cycloaddition of Tetrahydroisoquinolines, Aldehydes, and Ethyl Ketomalonate
A chemoselective and diastereoselective synthesis of fused oxazolidines was achieved by a three-component cascade reaction of tetrahydroisoquinolines (THIQs), α,β-unsaturated aldehydes, and diethyl 2-oxomalonate. Probably due to the reactivity difference between the aldehyde and the ketone, the reac...
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| Veröffentlicht in: | Journal of organic chemistry 2020-05, Vol.85 (9), p.6216-6224 |
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| container_issue | 9 |
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| container_title | Journal of organic chemistry |
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| creator | Wu, Xiang Zhu, Zheng-Hao He, Hao Ren, Lei Zhu, Cheng-Feng Li, You-Gui |
| description | A chemoselective and diastereoselective synthesis of fused oxazolidines was achieved by a three-component cascade reaction of tetrahydroisoquinolines (THIQs), α,β-unsaturated aldehydes, and diethyl 2-oxomalonate. Probably due to the reactivity difference between the aldehyde and the ketone, the reaction proceeded through the condensation of THIQs with α,β-unsaturated aldehydes and 1,3-dipolar cycloaddition of the generated azomethine ylide intermediate with 2-oxomalonate. The key features are easily available starting materials, mild reaction conditions, broad substrate scope, and high chemo- and diastereoselectivity. |
| doi_str_mv | 10.1021/acs.joc.0c00616 |
| format | Article |
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| title | Construction of 1,3-Oxazolidines through a Three-Component [3+2] Cycloaddition of Tetrahydroisoquinolines, Aldehydes, and Ethyl Ketomalonate |
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