Tetrahedron

Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes

JM Andrés, R Pedrosa, A Pérez, A Pérez-Encabo

Index: Andres, Jose M; Pedrosa, Rafael; Perez, Alberto; Perez-Encabo, Alfonso Tetrahedron, 2001 , vol. 57, # 40 p. 8521 - 8530

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Citation Number: 37

Abstract

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.