Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA.
Org Biomol Chem. 2021 Jan 6;19(1):46-81. doi: 10.1039/d0ob01938k.
Olefin 1,2-difunctionalization has emerged as a popular strategy within modern synthetic chemistry for the synthesis of vicinal amino alcohols and derivatives. The advantage of this approach is the single-step simplicity for rapid diversification, feedstock nature of the olefin starting materials, and the possible modularity of the components. Although there is a vast number of possible iterations of 1,2-olefin difunctionalization, 1,2-amino oxygenation is of particular interest due to the prevalence of both oxygen and nitrogen within pharmaceuticals, natural products, agrochemicals, and synthetic ligands. The Sharpless amino hydroxylation provided seminal results in this field and displayed the value in achieving methods of this nature. However, a vast number of new and novel methods have emerged in recent decades. This review provides a comprehensive review of modern advances in accomplishing 1,2-amino oxygenation of alkenes, 1,3-dienes, alkynes, and allenes that move beyond osmium to a range of other transition metals and more modern strategies such as electrochemical, photochemical, and biochemical reactivity.
烯烃 1,2-双官能化已成为现代合成化学中一种流行的策略，用于合成偕氨基醇和衍生物。这种方法的优点是单步简单，可快速多样化，烯烃起始原料具有原料性质，并且组件可能具有模块化。尽管 1,2-烯烃双官能化有大量可能的迭代，但由于在药物、天然产物、农用化学品和合成配体中普遍存在氧和氮，因此 1,2-氨基氧化特别有趣。Sharpless 氨基羟化在该领域提供了开创性的结果，并显示了实现这种性质的方法的价值。然而，近几十年来出现了大量新的和新颖的方法。这篇综述全面介绍了在实现烯烃、1,3-二烯、炔烃和烯丙基的 1,2-氨基氧化方面的现代进展，这些进展超越了锇，涉及到一系列其他过渡金属和更现代的策略，如电化学、光化学和生物化学反应性。
