Stereoselective Sequential Spirocyclopropanation/Cloke-Wilson Rearrangement Reactions for Synthesis of trans-β,γ-Disubstituted γ-Butyrolactones Using Alkylidene Meldrum's Acid and Benzyl Halides.,The Journal of Organic Chemistry

当前位置： X-MOL 学术 › J. Org. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Stereoselective Sequential Spirocyclopropanation/Cloke-Wilson Rearrangement Reactions for Synthesis of trans-β,γ-Disubstituted γ-Butyrolactones Using Alkylidene Meldrum's Acid and Benzyl Halides.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-22 , DOI: 10.1021/acs.joc.9b02978
Minli Zhang ₁ , Tong Li ₁ , Chaoxing Cui ₁ , Xixi Song ₁ , Junbiao Chang ₁

Affiliation

The stereoselective sequential spirocyclopropanation/Cloke-Wilson rearrangement reactions have been developed to synthesize γ-butyrolactones using alkylidene Meldrum's acids and benzyl halides. The DBU-promoted spirocyclopropanation was carried out efficiently at room temperature to generate trans-isomeric spirocyclopropyl Meldrum's acid, and the following stereospecific thermal decarboxylative Cloke-Wilson rearrangement afforded trans-γ-butyrolactones. A variety of aromatic and aliphatic Meldrum's acid derived olefins and benzyl halides were tolerated. Various trans-β,γ-disubstituted γ-butyrolactones were produced with moderate to good overall yields from 46 to 96% and excellent diastereoselectivities.

中文翻译：

立体选择性顺序螺环丙烷化/克-威尔逊重排反应，用于利用亚炔基Meldrum的酸和苄基卤化物合成反式β，γ-二取代的γ-丁内酯。

已经开发了立体选择性顺序螺环丙烷化/ Cloke-Wilson重排反应以使用亚烷基梅德鲁姆酸和苄基卤化物合成γ-丁内酯。在室温下有效地进行DBU促进的螺环丙烷化反应，生成反式异构的螺环丙基Meldrum酸，随后进行立体定向热脱羧Cloke-Wilson重排，得到反式γ-丁内酯。可以耐受多种芳香族和脂肪族Meldrum酸衍生的烯烃和苄基卤化物。生产了各种反式-β，γ-二取代的γ-丁内酯，总收率中等至良好，为46％至96％，非对映选择性极好。

更新日期：2020-01-23

点击分享查看原文

点击收藏

阅读更多本刊新发论文