1,3-stereoinduction in radical additions to glyoxylate imines

Synlett

Volumn , Issue 7, 1998, Pages 780-782

  Bertrand, Michèle P ^a   Feray, Laurence ^a   Nouguier, Robert ^a   Stella, Lucien ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001342149     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1763     Document Type: Article

References (57)

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53. 2 (2 ml). The mixture was stirred while air (1 ml) was added over 1 h with a syringe pump. The reaction was monitored by TLC. After completion the solution was concentrated and the residue was purified by chromatography on silica gel (5% EtOAc/pentane). This led to 2 as a 70:30 mixture of diastereomers (93 mg, 48%). When the same experiment was carried out without additional air the reaction needed 6 h to be completed.
54. 5,6-Dihydro-1,4-oxazin-2-ones are known to dimerize under irradiation in isopropanol, via captodative radicals (see : Gaudiano, J.; Frank, E.; Wysor, M.; Averbuch, S.; Koch, T. H. J. Org. Chem. 1993, 58, 7355 and previous refs therein). No dimeric products were identified in our experiments.
55. • in 22% yield. It is likely that the addition of the tertiary radical to the cyclic imine is slow compared to the competitive reduction by tin hydride.
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