6533b852fe1ef96bd12aab1a

RESEARCH PRODUCT

Stereocontrolledα-Alkylation of Fully ProtectedL-Serine

Thomas StraubMartin BrunnerAri M. P. KoskinenKari RissanenPauli Saarenketo

subject

chemistry.chemical_compoundStereochemistryChemistryOrganic ChemistryDiastereomerSubstituentStereoselectivityL serinePhysical and Theoretical ChemistryAlkylationRing (chemistry)Two-dimensional nuclear magnetic resonance spectroscopy

description

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. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

yearjournalcountryeditionlanguage
2004-09-01European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.200400207