Radical deuteration of α-selenylated-β-silylsulfoxides

Tetrahedron Letters

Volumn 38, Issue 2, 1997, Pages 233-236

  Angelaud, Rémy ^a   Landais, Yannick ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DEUTERIUM; ORGANOSELENIUM DERIVATIVE; SULFOXIDE;

ARTICLE; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0031021214     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02307-6     Document Type: Article

References (27)

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2. (b) Smadja, W. Synlett, 1994, 1-26.
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19. Opposite sense of stereoselectivity has been repeatedly observed during electrophilic functionalization of allylic (and homoallylic) alcohols and silanes: (a) Andrey, O.; Landais, Y. Tetrahedron Lett., 1993, 34, 8435-8438;
20. (b) Fleming, I. Pure & Appl. Chem., 1988, 60, 71-78 and references cited therein;
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23. 6
24. 2J See also: Pasto, D.J.; Krasnansky, R.; Zercher, C. J. Org. Chem., 1987, 52, 3062-3072.
25. 6a-b were prepared from commercial 3,3-dimethylbutanoic acid, according to the following sequence : Equation presented
26. 3 group since the C-C bond (1.54Å) is shorter than the C-Si bond (1.9Å).
27. On the opposite, a τ-Bu group was found to provide no stability to open chain carbon-centered radicals, see : Zhang, S.; Bordwell, F.G. J. Org. Chem., 1996, 61, 51-54 and references cited therein.