Organic letters

An expedient procedure for the oxidative cleavage of olefinic bonds with PhI (OAc) 2, NMO, and catalytic OsO4

KC Nicolaou, VA Adsool, CRH Hale

Index: Nicolaou; Adsool, Vikrant A.; Hale, Christopher R. H. Organic Letters, 2010 , vol. 12, # 7 p. 1552 - 1555

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Citation Number: 79

Abstract

PhI (OAc) 2 in the presence of OsO4 (cat.) and 2, 6-lutidine cleaves olefinic bonds to yield the corresponding carbonyl compounds, albeit, in some cases, with α-hydroxy ketones as byproduct. A more practical and clean protocol to effect oxidative cleavage of olefinic bonds involves NMO, OsO4 (cat.), 2, 6-lutidine, and PhI (OAc) 2.