Dialkylzinc mediated radical additions to chiral N-enoyloxazolidinones in the presence of benzaldehyde. Mechanistic investigation, structural characterization of the resulting γ-lactones

Tetrahedron

Volumn 61, Issue 17, 2005, Pages 4261-4274

  Bazin, Samantha ^a   Feray, Laurence ^a   Vanthuyne, Nicolas ^a   Bertrand, Michèle P ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Diethylzinc; N Enoyloxazolidinones; Radical polar crossover reaction; Lactones

Indexed keywords

BENZALDEHYDE; DIISOPROPYLZINC; FUMARIC ACID; GAMMA LACTONE DERIVATIVE; IODIDE; IODINE; N ENOYLOXAZOLIDINONE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; LACTONIZATION; PRIORITY JOURNAL; RADICAL REACTION; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 16244417479     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.042     Document Type: Article

References (47)

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36. -.
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46. Supporting Information content: Chiral HPLC analyses of racemic and optically pure lactones 9 and 22 (S2-S5), of lactones 15, 16, 17, 18, 19 and 20 (S6), detailed chiral HPLC conditions (S7). Significant NOESY correlations for lactones 9 and 15-20 (S8).
47. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 257463 for lactone 3, 257464 for lactone 4, 257465 for lactone 5, and 257466 for lactone 18. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].