Stereoselective a-alkylation of fully protected L-serine

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A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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Date
2004
Major/Subject
Mcode
Degree programme
Language
en
Pages
3879-3883
Series
European Journal of Organic Chemistry
Abstract
Diastereoselective alkylation of the (2S,4S) and (2R,4S) diastereomers of 3-tert-butyl 4-methyl 2-tert-butyl-1,3-oxazolidine-3,4-dicarboxylate (1a/b) is reported. Formation of both diastereomers of these oxazolidines was achieved by changing the order of protection steps, and their relative and absolute configurations were determined by NOESY spectroscopy. The use of the bulky ring substituent tBu together with Boc as the N-protecting group led to the exclusive formation of only one alkylated diastereomer.
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Keywords
L-serine, NOESY, stereoselective
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Citation
Koskinen , A M P , Saarenketo , P & Straub , T 2004 , ' Stereoselective a-alkylation of fully protected L-serine ' , European Journal of Organic Chemistry , pp. 3879-3883 . https://doi.org/10.1002/ejoc.200400207