Asymmetric Synthesis of Protected α-Amino Boronic Acid Derivatives with an Air- and Moisture-Stable Cu(II) Catalyst
Asymmetric Synthesis of Protected α-Amino Boronic Acid Derivatives with an Air- and Moisture-Stable Cu(II) Catalyst
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DOI：
10.1021/jo500300t
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发表时间：
2014-04-18
影响因子：
3.6
通讯作者：
Ellman, Jonathan A.
中科院分区：
文献类型：
--
作者：
Buesking, Andrew W.;Bacauanu, Vlad;Ellman, Jonathan A.
使用 Cu(II) 催化剂实现 N-叔丁亚磺酰亚胺与双（频哪醇）二硼的不对称硼基化，并提供了合成有用且药学相关的 α-氨基硼酸衍生物的途径。 Cu(II) 催化的反应是在室温下、空气中、使用市售的廉价试剂在低催化剂负载量下在台式上进行的。各种 N-叔丁亚磺酰亚胺（包括酮亚胺）很容易反应，以良好的产率和高立体选择性提供 α-亚磺酰氨基硼酸酯。此外，这种转化还适用于α-亚磺酰胺基三氟硼酸盐的直接、伸缩合成。
The asymmetric borylation of N-tert-butanesulfinyl imines with bis(pinacolato)diboron is achieved using a Cu(II) catalyst and provides access to synthetically useful and pharmaceutically relevant alpha-amino boronic acid derivatives. The Cu(II)-catalyzed reaction is performed on the benchtop in air at room temperature using commercially available, inexpensive reagents at low catalyst loadings. A variety of N-tert-butanesulfinyl imines, including ketimines, react readily to provide alpha-sulfinamido boronate esters in good yields and with high stereoselectivity. In addition, this transformation is applied to the straightforward, telescoped synthesis of alpha-sulfinamido trifluoroborates.