Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO(3)H generated "in situ" by oxidation of (PhSe)(2) with (NH(4))(2)S(2)O(8) at reflux in a 3:1 mixture of MeCN-H(2)O. Interestingly the reaction can be performed in "one pot" using a catalytic amount of diselenide affording the corresponding diols (5 and 6) with good yield and good level of diastereo- and enantioselectivity.
Diastereo and Enantioselective Synthesis of 1,2-Diols Promoted by Electrophilic Selenium Reagents
SANTI, Claudio;TIECCO, Marcello;TESTAFERRI, Lorenzo;TOMASSINI, Cristina;SANTORO, STEFANO;
2008
Abstract
Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO(3)H generated "in situ" by oxidation of (PhSe)(2) with (NH(4))(2)S(2)O(8) at reflux in a 3:1 mixture of MeCN-H(2)O. Interestingly the reaction can be performed in "one pot" using a catalytic amount of diselenide affording the corresponding diols (5 and 6) with good yield and good level of diastereo- and enantioselectivity.File in questo prodotto:
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