A Highly Stereoselective Synthesis of Chiral α-Amino-β-lactams via the Kinugasa Reaction Employing Ynamides

A highly stereoselective synthesis of chiral α-amino-β-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.

本文报道了一种通过炔酰胺（ynamide）-衣谷佳反应（Kinugasa）合成手性α-氨基-β-内酰胺的高立体选择性方法。此外，本文还阐明了一种机理模型，用以合理化所观测到的非对映选择性：该选择性同时取决于初始的[3+2]环加成步骤与后续的质子化过程，且这两个步骤均具有高度选择性。