Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.
J Org Chem. 2014 Apr 18;79(8):3671-7. doi: 10.1021/jo500300t. Epub 2014 Mar 31.
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 α-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 α-sulfinamido boronate esters in good yields and with high stereoselectivity. In addition, this transformation is applied to the straightforward, telescoped synthesis of α-sulfinamido trifluoroborates.
N-叔丁基亚磺酰亚胺的不对称硼化反应是通过使用 Cu(II)催化剂和双(频哪醇)二硼来实现的，这为合成有用的和具有药物相关性的α-氨基硼酸衍生物提供了一种方法。该 Cu(II)催化反应在室温下在空气中使用商业上可获得的、廉价的试剂在低催化剂负载下在实验台上进行。各种 N-叔丁基亚磺酰亚胺，包括酮亚胺，反应迅速，以高立体选择性和良好的收率提供α-磺酰胺基硼酸酯。此外，这种转化被应用于α-磺酰胺基三氟硼酸盐的直接、缩合合成。
