Manganese-promoted regioselective ring-opening of 2,3-epoxy acid derivatives: a new route to α-hydroxy acid derivatives
A simple and general methodology directed towards the synthesis 3-aryl-2-hydroxy amides, or esters with total regioselectivity from the easily available 2,3-epoxy amides or esters, promoted by active manganese is described. Utilizing enantiopure epoxy amides as starting materials, the corresponding 3-aryl-2-hydroxy amides in enantiopure form are also available. Some synthetic applications of selected examples of 3-aryl-2-hydroxy carboxylic acid derivatives are shown. A mechanism has been proposed to explain this novel reaction.
Concellon, Jose M.,Bernad, Pablo L.,Rodriguez-Solla, Humberto,Diaz, Pamela
experimental part
p. 2178 - 2184
(2009/12/31)
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