Synthesis and lithiation of oxazolinylaziridines: The N-substituent effect

Tetrahedron

Volumn 61, Issue 13, 2005, Pages 3251-3260

  Luisi, Renzo ^a   Capriati, Vito ^a   Florio, Saverio ^a   Di Cunto, Peppino ^a   Musio, Biagia ^a  

^a NONE

Author keywords

Aziridino lactones; Aziridinyllithiums; Lithiation; Oxazolinylaziridines

Indexed keywords

AZIRIDINE DERIVATIVE; CARBONYL DERIVATIVE; LITHIUM DERIVATIVE; OXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; LITHIATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 14844336389     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.045     Document Type: Article

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33. An X-ray analysis confirmed the structure of the oxazolinylaziridine (R*,R*)-3b and the configuration at the aziridine nitrogen. Crystallographic data (excluding structure factors) for (R*,R*)-3b have been deposited to the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 249586. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: 144-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].
34. The configuration of aziridines 6 (R*,R*) was assigned on the basis of the chemical shift of the Me (to the oxazolinyl ring either by analogy to similar trisubstituted oxazolinylaziridines, as reported in Ref.17a, or by analogy to compounds 3b-D and 4b-D. A Ph group in a cis relationship with a Me group (R*,R* isomers) was found to induce a high field displacement on it (chemical shift range: 1.30-1.40 (δ); in the case of a trans relationship (R*,S* isomers) the Me group was always downfield shifted (chemical shift range: 1.70-1.80 (δ).
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