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N ‐Methylpyrrolidone Hydroperoxide/Cs 2 CO 3 as an Excellent Reagent System for the Hydroxy‐Directed Diastereoselective Epoxidation of Electron‐Deficient Olefins
Author(s) -
Victor Napoleon John,
Gana Janardhanan,
Muraleedharan Kannoth Manheri
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501929
Subject(s) - chemoselectivity , reagent , chemistry , sulfur , base (topology) , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , mathematical analysis , mathematics
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.