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Royal Society of Chemistry, Journal of the Chemical Society, Chemical Communications, 18, p. 1313

DOI: 10.1039/c39910001313

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Homologation ofL-threonine to α-epimer β-amino-α,γ-dihydroxy aldehydes and acids via stereoselective reduction of 2-thiazolyl amino ketones

Journal article published in 1991 by Alessandro Dondoni, Daniela Perrone ORCID, Pedro Merino
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

The differentially protected 2-thiazolyl amino ketones 3 and 7 obtained in high yield from the L-threonine derived methyl ester 2 and 2-lithiothiazole serve as key intermediates to aldehydes 6 and 11 by syn- and anti-stereoselective reduction (diastereoselectivity 95%) of the carbonyl and liberation of the formyl group from the thiazole ring; the latter compounds are smoothly oxidized to acids 12 and 13.