New Synthesis of Optically Active 5-Isoxazolidinones and β-Amino Acids

Journal of Organic Chemistry

Volumn 68, Issue 25, 2003, Pages 9861-9864

  Luisi, Renzo ^a,b   Capriati, Vito ^a,b   Florio, Saverio ^a,b   Vista, Teresa ^a,b  

^a UNIVERSITY OF BARI   (Italy)

^b ICCOM CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSELECTIVE SYNTHESIS;

NITROGEN COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

2 ISOPROPYL 2 OXAZOLINE; 5 ISOXAZOLIDINONE; BETA AMINO ACID; ISOXAZOLIDINE DERIVATIVE; NITRONE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHIRALITY; CRYSTALLIZATION; DIASTEREOISOMER; ENANTIOMER; LITHIATION; METHODOLOGY; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; HETEROCYCLIC COMPOUNDS; MODELS, CHEMICAL; NITROGEN OXIDES; OXAZOLIDINONES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 0344235333     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035356i     Document Type: Article

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8. 1H NMR spectra as well (see the Supporting Information).
9. In the course of the reduction of 6b the chlorine atom was lost and 7a was the only isolated product. There are other cases concerning the loss of a halogen atom under reduction conditions, see: McQuillin, F. J.; Ord, W. O. J. Am. Chem. Soc. 1959, 81, 9-3172.
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11. 3 or acidic solution to the corresponding spirocyclic form whose hydrolysis gave the 5-isoxazolidinone (-)-6a (er determinated by chiral GC, see the Supporting Information).
12. The X-ray analysis of (R,R,R)-12a allowed the determination of the absolute configuration at the newly created stereogenic centers. CCDC-213766 contain the supplementary crystallographic data for compound (R,R,R)-12a. These data can be obtained free of charge at www.ccdc.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (int) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk.
13. The er value of 5-isoxazolidinones (-)-6a,b were determined by chiral GC on a β-cyclodextrin capillary column. The retention time of (-)-6a was the same observed in the case of the 5 -isoxazolidinone derived from the hydrolysis of (R,R)-10, thus confirming its absolute configuration (R) at C-3.
14. 5-Isoxazolidinone (-)-6b was tentatively assigned the R configuration by comparison of its GC retention time (first eluted) and the sign of its optical rotation with those of the known (-)-6a (see the Supporting Information).
15. 13C NMR spectrum are diagnostic of the presence of the hydroxylamino form (S,S)-14.
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