An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids
An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids
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DOI：
10.1021/jo202221c
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发表时间：
2012-01-20
影响因子：
3.6
通讯作者：
Yeung, Ying-Yeung
中科院分区：
文献类型：
--
作者：
Chen, Jie;Zhou, Ling;Yeung, Ying-Yeung
建立了3，4-二氢异香豆素的一种简便的对映选择性合成方法。该方法涉及氨基硫代氨基甲酸酯催化的苯乙烯类羧酸的对映体选择性溴代环化反应，以较高的产率和ee‘s合成3-溴-3，4-二氢异香豆素。3-溴-3，4-二氢异香豆素是多种二氢异香豆素衍生物的通用构筑块，其中的BR基团可以很容易地被修饰以获得具有重要生物意义的4-O型和4-N型3，4-二氢异香豆素体系。此外，研究表明，通过精制一些工艺参数，可以得到产率和ee均较好的合成有用的5-外苯酞产品。
A facile and enantioselective approach toward 3,4-dihydroisocoumarin was developed. The method involved an amino-thiocarbamate catalyzed enantioselective bromocyclization of styrene-type carboxylic acids, yielding 3-bromo-3,4-dihydroisocoumarins with good yields and ee's. 3-Bromo-3,4-dihydroisocoumarins are versatile building blocks for various dihydroisocoumarin derivatives in which the Br group can readily be modified to achieve biologically important 4-O-type and 4-N-type 3,4-dihydroisocoumarin systems. In addition, studies indicated that, by refining some parameters, the synthetically useful 5-exo phthalide products could be achieved with good yields and ee's.