Tetrahedron letters

An efficient enantiomeric three step synthesis of β-amino acids (esters)

MK Mokhallalati, MJ Wu, LN Pridgen

Index: Mokhallalati, Mohamed K.; Wu, Ming-Jung; Pridgen, Lendon N. Tetrahedron Letters, 1993 , vol. 34, # 1 p. 47 - 50

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Citation Number: 32

Abstract

Abstract Ethyl tributylstannylacetate was reacted with (R)-2-aryl or alkyl-1, 3-oxazolidines 6 under very specific (ZnCl 2/Et 2 O· BF 3, 0.5 equiv each) Lewis Acid catalysed conditions to yield (1R, 1′ R)-N-2′-hydroxy-1′-phenylethyl-1-aryl or alkyl-2-carboethoxyethylamine 8 in 91–99% de. The amino alcohol products 8 were converted to aromatic and aliphatic β- amino esters 9, useful precursors to β-lactams.

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