Auto-tandem catalysis: facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloaddition-elimination reaction

Auto-tandem catalysis: facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloaddition-elimination reaction
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DOI:
10.1039/c0cc03336g
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发表时间:
2010-01-01
影响因子:
4.9
通讯作者:
Takemoto, Yoshiji
Takemoto, Yoshiji
中科院分区:
化学2区
文献类型:
--
作者:
Takasu, Kiyosei;Tanaka, Toru;Takemoto, Yoshiji

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描述了由3-氧甲基-2-甲硅烷氧基-1,3-丁二烯和α,β-不饱和酮制备取代的2-亚烷基-环己酮的催化多米诺反应,所述3-氧甲基-2-甲硅烷氧基-1,3-丁二烯可由Baylis-Hillman加合物制备。该过程涉及两个不同的反应机理,(4+2)环加成和消除。这两个反应都是由Tf 2NH催化的。
A catalytic domino reaction producing substituted 2-alkylidene-cyclohexanone from 3-oxymethyl-2-siloxy-1,3-butadienes, which can be prepared from Baylis-Hillman adducts, and alpha, beta-unsaturated ketones is described. The process involves two mechanistically distinct reactions, (4+2) cycloaddition and elimination. Both of these reactions are catalyzed by Tf2NH.