Lithiation of optically active oxazolinyloxiranes: Configurational stability

Tetrahedron

Volumn 59, Issue 49, 2003, Pages 9707-9712

  Luisi, Renzo ^a   Capriati, Vito ^a   Carlucci, Claudia ^a   Degennaro, Leonardo ^a   Florio, Saverio ^a  

^a Dipartimento di Fisica   (Italy)

Author keywords

Configuration; Lithiation; Oxazolines; Oxiranes; Stereochemistry

Indexed keywords

2 CHLOROMETHYL 4 ISOPROPYL 2 OXAZOLINE; 2 METHYL 1 (4 ISOPROPYL 4,5 DIHYDROOXAZOL 2 YL) 1,2 EPOXYPROPANE; 4 ISOPROPYL 2 (1 OXASPIRO[2.5]OCT 2 YL) 4,5 DIHYDROOXAZOLE; 4 ISOPROPYL 2 (3 PHENYLOXIRANYL) 4,5 DIHYDROOXAZOLE; ACETONE; ETHYLENE OXIDE DERIVATIVE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; LITHIATION; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 0242558740     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.018     Document Type: Article

References (26)

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21. Oxazolinyloxiranes 3a,b could be assigned the S configuration at the oxiranyl stereogenic centre by analogy to the oxazolinyloxiranes previously prepared by such a methodology, see Ref. 5.
22. 1H NMR of the diastereomeric mixture prepared as reported in Ref. 8.
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24. 1H NMR spectra but have different optical rotations (see Section 4), therefore 3g should have a (4S,2′R,3′S) configuration. The latter also derive from an α-epimerization involving lithiated cis-3e whose absolute configuration should be therefore (4S,2′S,3′S). The last diastereomer cis-3f, by exclusion, should have necessarily a (4S,2′R,3′R) configuration.
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