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

Add time:09/02/2019    Source:sciencedirect.com

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.

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