Chemical Genomics Center of the Max Planck Society , Dortmund 44227 , Germany.
Department of Chemical Biology , Max Planck Institute of Molecular Physiology , Dortmund 44227 , Germany.
Chem Rev. 2019 Oct 23;119(20):11245-11290. doi: 10.1021/acs.chemrev.9b00214. Epub 2019 Aug 27.
The Petasis boron-Mannich reaction, simply referred to as the Petasis reaction, is a powerful multicomponent coupling reaction of a boronic acid, an amine, and a carbonyl derivative. Highly functionalized amines with multiple stereogenic centers can be efficiently accessed via the Petasis reaction with high levels of both diastereoselectivity and enantioselectivity. By drawing attention to examples reported in the past 8 years, this Review demonstrates the breadth of the reactivity and synthetic applications of Petasis reactions in several frontiers: the expansion of the substrate scope in the classic three-component process; nonclassic Petasis reactions with additional components; Petasis-type reactions with noncanonical substrates, mechanism, and products; new asymmetric versions assisted by chiral catalysts; combinations with a secondary or tertiary transformation in a cascade- or sequence-specific manner to access structurally complex, natural-product-like heterocycles; and the synthesis of polyhydroxy alkaloids and biologically interesting molecules.
佩特阿斯硼-曼尼希反应，简称佩特阿斯反应，是一种硼酸、胺和羰基衍生物的多组分偶联反应。通过佩特阿斯反应，可以高效地获得具有多个立体中心的高官能化胺，并且具有高的非对映选择性和对映选择性。本文通过关注过去 8 年报道的实例，展示了佩特阿斯反应在几个前沿领域的反应性和合成应用的广泛性：经典三组分过程中底物范围的扩展；具有额外组分的非经典佩特阿斯反应；具有非典型底物、机理和产物的佩塔斯基型反应；在手性催化剂辅助下的新不对称版本；与二级或三级转化以级联或序列特异性方式组合，以获得结构复杂、类似天然产物的杂环；以及多羟基生物碱和生物感兴趣分子的合成。
