Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes
N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-γ-dibenzylamino-β-hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding γ-amino-β-hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-γ-tert-butoxycarbonylamino-β-hydroxy esters as the major product.
Andrés, José M,Pedrosa, Rafael,Pérez, Alberto,Pérez-Encabo, Alfonso
p. 8521 - 8530
(2007/10/03)
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