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Diastereoselective formation of highly functionalised α-substituted amino acid derivatives via aldol addition

✍ Scribed by Martin Brunner; Maija Nissinen; Kari Rissanen; Thomas Straub; Ari M.P. Koskinen

Publisher: Elsevier Science
Year: 2005
Tongue: English
Weight: 170 KB
Volume: 734
Category: Article
ISSN: 0022-2860
DOI: 10.1016/j.molstruc.2004.09.020

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✦ Synopsis

Highly diastereoselective aldol additions of (2R,4S)-3-tert-butyl 4-methyl 2-tert-butyloxazolidine-3,4-dicarboxylate (1) are reported. The utility of the highly substituted oxazolidines of type 1 for diastereoselective a-addition of the fully protected amino acid L-serine with achiral and chiral carbonyl compounds is demonstrated and the relative and absolute configuration of the aldol products are discussed on the basis of NOESY data and solid state structures of selected examples. The aldol products represent highly useful intermediates in the syntheses of sphingosine-related metabolites.

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