New Osmium-Based Reagent for the Dihydroxylation of Alkenes

The cis dihydroxylation of alkenes is most efficiently accomplished by reaction with osmium tetroxide.
Recently, the expense and toxicity of osmium tetroxide have led to a number of attempts to harness
alternative osmium-based reagents, including microencapsulation and solid support techniques. We describe
here the development of a new nonvolatile, stable, and recoverable osmium-based reagent devised for
the stoichiometric cis dihydroxylation of alkenes. Although attempts to make this new dihydroxylation
work with catalytic amounts of this reagent were unsuccessful, we did develop a sensitive test for free
osmium tetroxide leached from the reagent in situ:  this test may well have uses in probing future
applications of derivatized osmium reagents.

烯烃的顺式二羟基化反应，通过与四氧化锇的反应最为高效。近期，鉴于四氧化锇的成本与毒性，研究者们尝试利用包括微胶囊化和固体载体技术在内的多种替代性锇基试剂。本文详细阐述了新型非挥发性、稳定性强且可回收的锇基试剂的开发，该试剂专为烯烃的等摩尔顺式二羟基化反应设计。尽管尝试以催化量使用该试剂进行新的二羟基化反应未果，但我们成功开发了一种对位处试剂中的游离四氧化锇进行原位检测的敏感测试方法：此测试方法或许在探索未来衍生化锇基试剂的应用中具有潜在用途。