Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source

Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source
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DOI:
10.1021/ja028518l
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发表时间:
2002-12-18
影响因子:
15
通讯作者:
Rudolph, J
Rudolph, J
中科院分区:
化学1区
文献类型:
--
作者:
Bolm, C;Rudolph, J

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手性二芳基甲醇是合成生物活性化合物的重要中间体。在这里,我们描述了一种从容易获得的起始材料催化不对称合成的灵活方法。值得注意的是,使用单一催化剂,只需选择芳基硼酸或醛分别作为芳基供体和受体的适当组合即可获得产物的两种对映体。平面手性二茂铁的催化很容易进行,并产生多种具有优异对映选择性(高达 98% ee)的产品。
Chiral diaryl methanols are important intermediates for the synthesis of biologically active compounds. Here, we describe a flexible method for their catalyzed asymmetric synthesis from readily available starting materials. Noteworthy is the fact that with a single catalyst both enantiomers of the product are accessible simply by choosing the appropriate combination of aryl boronic acid or aldehyde as aryl donor and acceptor, respectively. The catalysis with a planar-chiral ferrocene is easy to perform and yields a broad range of products with excellent enantioselectivities (up to 98% ee).