Asymmetric synthesis of homoallylic amines via 1,2-addition of Grignard reagent to aliphatic N-phosphonyl hemiaminal

作者：Qiao, Shuo; Pindi, Suresh; Spigener, Preston T.; Jiang, Bo; Li, Guigen^*

来源：Tetrahedron Letters, 2016, 57(5): 619-622.

DOI：10.1016/j.tetlet.2015.12.106

• Alkylated homoallylic amines
• N-Phosphonyl amides
• 1,2-Nucleophilic addition
• N-Phosphonyl imines
• Group-assisted-purification (GAP)

A general method for asymmetric synthesis of alkylated homoallylic amines was developed via a one-pot three-component reaction of easily available N-phosphonyl amides, aliphatic aldehydes, and allylic Grignard reagents. As anticipated the reaction proceeds through six-membered chelation controlled mechanism, allowing 1,2-nucleophilic addition to directly give chiral homoallylic amines with high yields and excellent diastereoselectivity.

• 出版日期2016-2-3
• 单位南京大学