Department of Chemistry, Yale University , New Haven, Connecticut 06520-8107, USA.
Org Lett. 2011 Mar 4;13(5):964-7. doi: 10.1021/ol103002t. Epub 2011 Feb 9.
The MgCl(2)-enhanced addition of benzyl zinc reagents to N-tert-butanesulfinyl imines proceeds readily at room temperature to afford the N-tert-butanesulfinyl-protected amine products in good yields and diastereomeric ratios. This method is functional group tolerant in both the imine substrate and benzyl zinc coupling partner. Moreover, benzyl zinc reagent addition to the N-tert-butanesulfinyl imine 3o prepared from isopropylidene-protected glyceraldehyde proceeds in high yield and with exceptional selectivity to provide rapid entry to hydroxyethylamine-based aspartyl protease inhibitors.
氯化镁增强的 N-叔丁基亚磺酰亚胺与苄基锌试剂的加成反应在室温下即可顺利进行，以高收率和优异的非对映选择性得到 N-叔丁基亚磺酰基保护的胺产物。该方法对亚胺底物和苄基锌偶联试剂均具有官能团耐受性。此外，N-叔丁基亚磺酰亚胺 3o 由异亚丙基甘油醛制备而来，其与苄基锌试剂的加成反应以高产率和出色的选择性进行，为基于羟乙基胺的天冬氨酸蛋白酶抑制剂提供了快速入口。
