Victor Napoleon John, Gana Janardhanan, Muraleedharan Kannoth Manheri
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India, Fax: (+91)-44 2257 4202.
Chemistry. 2015 Oct 12;21(42):14742-7. doi: 10.1002/chem.201501929. Epub 2015 Aug 27.
This report introduces N-methylpyrrolidone hydroperoxide (NMPOOH)/base as an excellent reagent system for hydroxy-directed syn selective epoxidation of electron-deficient olefins, characterized by high diastereoselectivity, short reaction times and remarkable chemoselectivity, especially in presence of oxidatively labile nitrogen or sulfur atoms. NMPOOH also proves efficient in the oxidation of electron-deficient aromatic aldehydes, in the removal of oxazolidinone chiral auxiliary, and in the functionalization of alkenes and alkynes, showing wide application potential.
本报告介绍了N-甲基吡咯烷酮氢过氧化物（NMPOOH）/碱作为一种用于缺电子烯烃羟基导向的顺式选择性环氧化的优异试剂体系，其特点是具有高非对映选择性、短反应时间和显著的化学选择性，特别是在存在氧化不稳定的氮或硫原子的情况下。NMPOOH在缺电子芳香醛的氧化、恶唑烷酮手性助剂的去除以及烯烃和炔烃的官能化方面也证明是有效的，显示出广泛的应用潜力。
