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(Journal Article) |
Organic letters 16 (21): 5674-7 (2014)
I2-catalyzed regioselective oxo- and hydroxy-acyloxylation of alkenes and enol ethers: a facile access to α-acyloxyketones, esters, and diol derivatives.
Rambabu N Reddi
,
Pragati K Prasad
,
Arumugam Sudalai
ABSTRACT
I2-catalyzed oxo-acyloxylation of alkenes and enol ethers with carboxylic acids providing for the high yield synthesis of α-acyloxyketones and esters is described. This unprecedented regioselective oxidative process employs TBHP and Et3N in stoichiometric amounts under metal-free conditions in DMSO as solvent. Additionally, I2-catalysis allows the direct hydroxy-acyloxylation of alkenes with the sequential addition of BH3·SMe2 leading to monoprotected diol derivatives in excellent yields.