Boronic Acid-Catalyzed, Highly Enantioselective Aza-Michael Additions of Hydroxamic Acid to Quinone Imine Ketals

Boronic acid is one of the most versatile organic molecules in chemistry. Its uses include organic reactions, molecular recognition, assembly, and even medicine. While boronic acid catalysis, which utilizes an inherent catalytic property, has become an important research objective, it still lags far behind other boronic acid chemistries. Here, we report our discovery of a new boronic acid catalysis that enables the aza-Michael addition of hydroxamic acid to quinone imine ketals. By using 3-borono-BINOL as a chiral boronic acid catalyst, this reaction could be implemented in a highly enantio­selective manner, paving the way to densely functionalized cyclohexanes.

硼酸（boronic acid）是化学领域中用途最为广泛的有机分子之一，其应用涵盖有机反应、分子识别、分子组装乃至医药领域。尽管利用其固有催化特性的硼酸催化已成为重要的研究方向，但该领域仍远落后于其他硼酸化学分支。本研究报道了一种新型硼酸催化体系，可实现羟肟酸（hydroxamic acid）与醌亚胺缩酮（quinone imine ketals）之间的氮杂迈克尔加成（aza-Michael addition）反应。通过使用3-硼酸基联萘酚（3-borono-BINOL）作为手性硼酸催化剂，该反应可实现高对映选择性合成，为制备多官能团化环己烷开辟了新途径。