88425-34-7Relevant academic research and scientific papers
Serine as chiral educt for the practical synthesis of enantiopure N-protected β-hydroxyvaline
Dettwiler, James E.,Lubell, William D.
, p. 177 - 179 (2007/10/03)
N-tert-Butyloxycarbonyl- and N-benzenesulfonyl-β-hydroxyvalines 1a and 1b were, respectively, synthesized in enantiomerically pure form by a two-step protocol from their enantiomeric N-protected serine methyl esters 2a and 2b. The addition of CH3MgBr to 2a and 2b provided diols 3a and 3b, respectively as major products in 83% and 81% yields. Selective oxidation of diols 3a and 3b was performed using a TEMPO, NaClO2, NaOCl cocktail in 96% and 93% respective yields. This two-step process effectively furnished multigram amounts of enantiopure N-Boc-β-hydroxyvaline 1a.
Enantiospecific synthesis of 3-pyrrolines: A route to novel polyhydroxylated pyrrolidines
Burley, Ian,Hewson, Alan T.
, p. 7099 - 7102 (2007/10/02)
Enantiomer acetamido ketones are converted by an intramolecular Wittig reaction into enantiopure 3-pyrrolines; the product from (S)-serine provides access to novel polyhydroxylated pyrrolidines.
alpha -AMINO ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS. A GENERAL SYNTHESIS OF D- alpha -AMINO ACIDS FROM L-SERINE.
Maurer,Takahata,Rapoport
, p. 1095 - 1098 (2007/10/02)
A short and chirally efficient synthesis of four D- alpha -amino acids is described with L-serine as the chiral educt. The key C-C bond-forming reactions are the aminoacylations of organometallics with the lithium salt of N-(phenylsulfonyl)-L-serine (2) to give optically pure N-blocked alpha -amino ketones. Reduction of the carbonyl group to carbinol or methylene followed by oxidation of the hydroxymethyl to carboxyl gives the N-blocked D-amino acids. The examples investigated (norleucine, alpha -aminopimelic acid, DOPA, and allothreonine) demonstrate the broad applicability of the method.
