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. 2004 Jan 9;69(1):105-11.
doi: 10.1021/jo0302861.

Syntheses and reactions of optically active alpha-aminoallenylstannanes

Peter B D Ranslow  1 , Louis S Hegedus, Cristobal de los Rios
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Syntheses and reactions of optically active alpha-aminoallenylstannanes

Peter B D Ranslow et al. J Org Chem. .

Abstract

Lithiation/stannylation of optically active N-propargyloxazolidinones produced optically active alpha-oxazolidinonylallenylstannanes. Reaction of these with aldehydes in the presence of BF(3).OEt(2) produced beta-hydroxypropargylamines with high syn diastereoselectivity and ee. These were converted to gamma-hydroxy-beta-amino acids by oxidative cleavage of the alkyne.

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