N-heterocyclic carbene catalyzed additions of 3-trimethylsilyl propiolate to aldehydes

N-heterocyclic carbene catalyzed additions of 3-trimethylsilyl propiolate to aldehydes
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N-杂环卡宾催化3-三甲基甲硅烷基丙炔酸酯与醛的加成

DOI:
10.1016/j.jscs.2013.12.007
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发表时间:
2016-03
影响因子:
5.6
通讯作者:
He, Lin
He, Lin
中科院分区:
化学2区
文献类型:
--
作者:
Du, Guang-Fen;Zou, Xiao-Lei;Dai, Bin;He, Lin

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研究了n -杂环羰基(NHC)催化3-三甲基丙酸硅酯与醛的加成反应。在2mol % NHCs的催化下,苯甲醛、糠醛、β-萘醛、间代和对取代芳香醛与3-三甲基丙酸硅酯反应生成β-酰化MBH加合物,收率高,立体选择性好。而邻苯二甲酸取代苯甲醛与3-三甲基丙酸硅酯偶联得到的烷基化产物是相同反应条件下的唯一产物。
A N-heterocyclic carbene (NHC) catalyzed addition reaction of 3-trimethylsilyl propiolate with aldehydes has been developed. Under the catalysis of 2 mol% NHCs, benzaldehyde, furfural, β-naphthaldehyde,meta- andpara-substituted aromatic aldehydes reacted with 3-trimethylsilyl propiolate to afford β-acylated MBH adducts in good yield with excellent stereoselectivity. Whileortho-substituted benzaldehydes coupled with 3-trimethylsilyl propiolate to give alkynylation products as the sole products under the same reaction conditions.
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