ISSN:
0170-2041
Keywords:
α-Alkylation of amino acids
;
Self-regeneration of stereogenic centers
;
Oxazolidinones from amino acids and pivalaldehyde
;
Azetidine-derived (R,R)-α-amino-β-hydroxy carboxylic acid, X-ray crystal structure of
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The enolate generated from S-phenyl (S)-1-benzyl-2-azetidinecarbothioate is converted into racemic products 2 by treatment with electrophiles. The bicyclic oxazolidinone derivative 12 has been prepared from trimethylsilyl (S)-1-(trimethylsilyl)-2-azetidinecarboxylate (11) and pivalaldehyde without racemization. Addition of 12 to aldehydes and hydrolysis gives the products 13 a-h. The structure of the adduct 13 h from 4-pyridinecarbaldehyde was determined by X-ray crystal structure analysis, proving that the trigonal centers of the bicyclic enolate and of the aldehyde have combined with relative topicity unlike. Thus, the reaction resembles that of the homologous proline derivative described previously, and the novel products are formally D-allo-threonines with an ethylene bridge between the nitrogen and the adjacent carbon atoms (Scheme 4) and with absolute configuration R,R. The mechanism of the C — C bond-forming reaction is discussed.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1990199001129
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