有机化学 ›› 2021, Vol. 41 ›› Issue (11): 4467-4475.DOI: 10.6023/cjoc202105002 上一篇 下一篇
研究论文
收稿日期:
2021-05-01
修回日期:
2021-07-05
发布日期:
2021-07-26
通讯作者:
黄杰, 付振乾
基金资助:
Yuxia Zhanga, Jingcheng Guoa, Jie Huangb(), Zhenqian Fua()
Received:
2021-05-01
Revised:
2021-07-05
Published:
2021-07-26
Contact:
Jie Huang, Zhenqian Fu
Supported by:
文章分享
在氮杂环卡宾催化下, 乙酸酯和β-硅基烯酮发生[4+2]环合反应, 可高立体选择性地合成具有潜在应用价值的β-硅基δ-内酯类化合物. 该方法具有底物简单易得、反应条件温和、底物普适性好和操作简单等优点, 且反应规模放大10倍后也得到了优异的产率和对映体选择性. 该反应产物在氢化还原反应中均呈现出优良的实验结果, 可转化为降血脂药Ezetimibe.
张雨霞, 郭京程, 黄杰, 付振乾. 氮杂环卡宾催化乙酸酯和β-硅基烯酮的[4+2]环合反应:高立体选择性合成β-硅基δ-内酯[J]. 有机化学, 2021, 41(11): 4467-4475.
Yuxia Zhang, Jingcheng Guo, Jie Huang, Zhenqian Fu. N-Heterocyclic Carbene-Catalyzed [4+2] Annulation of Acetates and β-Silyl Enones: Highly Enantioselective Synthesis of β-Silyl δ-Lactones[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4467-4475.
Entry | NHC | 1 | Base | Solvent | Yieldb/% | eec/% |
---|---|---|---|---|---|---|
1 | A | 1a | DBU | THF | 44 | — |
2 | B | 1a | DBU | THF | 17 | 99 |
3 | B | 1b | DBU | THF | 88 | 99 |
3 | B | 1b | DBU | 1,4-Dioxane | 55 | 99 |
4 | B | 1b | DBU | CH3CN | 54 | 99 |
5 | B | 1b | DBU | TOL | 66 | 99 |
6 | B | 1b | DBU | DCM | 66 | 99 |
7 | B | 1b | DBU | CHCl3 | 57 | 99 |
8 | B | 1b | Et3N | THF | 50 | 99 |
9 | B | 1b | DIPEA | THF | 49 | 99 |
10 | B | 1b | K2CO3 | THF | 40 | 99 |
11 | B | 1b | DMAP | THF | 51 | 99 |
12 | B | 1b | DBN | THF | 85 | 99 |
13d | B | 1b | DBU | THF | 86 | 99 |
14e | B | 1b | DBU | THF | 74 | 99 |
15f | B | 1b | DBU | THF | 69 | 99 |
16d,g | B | 1b | DBU | THF | 80 | 99 |
Entry | NHC | 1 | Base | Solvent | Yieldb/% | eec/% |
---|---|---|---|---|---|---|
1 | A | 1a | DBU | THF | 44 | — |
2 | B | 1a | DBU | THF | 17 | 99 |
3 | B | 1b | DBU | THF | 88 | 99 |
3 | B | 1b | DBU | 1,4-Dioxane | 55 | 99 |
4 | B | 1b | DBU | CH3CN | 54 | 99 |
5 | B | 1b | DBU | TOL | 66 | 99 |
6 | B | 1b | DBU | DCM | 66 | 99 |
7 | B | 1b | DBU | CHCl3 | 57 | 99 |
8 | B | 1b | Et3N | THF | 50 | 99 |
9 | B | 1b | DIPEA | THF | 49 | 99 |
10 | B | 1b | K2CO3 | THF | 40 | 99 |
11 | B | 1b | DMAP | THF | 51 | 99 |
12 | B | 1b | DBN | THF | 85 | 99 |
13d | B | 1b | DBU | THF | 86 | 99 |
14e | B | 1b | DBU | THF | 74 | 99 |
15f | B | 1b | DBU | THF | 69 | 99 |
16d,g | B | 1b | DBU | THF | 80 | 99 |
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