title: N-Methylpyrrolidone Hydroperoxide/Cs2 CO3 as an Excellent Reagent System for the Hydroxy-Directed Diastereoselective Epoxidation of Electron-Deficient Olefins.
abstract: 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.
authors: Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India, Fax: (+91)-44 2257 4202.
authors: Napoleon John
authors: NJ
authors: Victor
authors: Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India, Fax: (+91)-44 2257 4202.
authors: Janardhanan
authors: J
authors: Gana
authors: Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India, Fax: (+91)-44 2257 4202. mkm@iitm.ac.in.
authors: Kannoth Manheri
authors: KM
authors: Muraleedharan
keywords: chemoselectivity; diastereoselectivity; epoxidation; oxidation; peroxides