Homologation ofL-threonine to α-epimer β-amino-α,γ-dihydroxy aldehydes and acids via stereoselective reduction of 2-thiazolyl amino ketones
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 18,p. 1313-1314
- https://doi.org/10.1039/c39910001313
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.Keywords
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