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Synlett 1996; 1996(9): 867-870
DOI: 10.1055/s-1996-5597
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Oxidation of 3-Tributylstannyl-1-alkenyl carbamates with Selenium Dioxide

David Madec, Jean-Pierre Férézou*
  • *Laboratoire de Synthèse Organique, (CNRS, URA 1308), DCSO, Ecole Polytechnique, F-91128 Palaiseau Cedex, France, Fax (33-1) 69 33 30 10, Bitnet ferezou@poly.polytechnique.fr
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Publikationsdatum:
31. Dezember 2000 (online)

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Selenium dioxide oxidation reaction of (Z)-3-tributylstannyl-1-alkenyl carbamates, easily obtained from allylic carbamates precursors via Buli/TMEDA/Ti(O i Pr)4 metallation, results in formation of the corresponding 3-hydroxy-1-alkenyl carbamates in high yield. No trace of the corresponding oxo derivatives was detected. Under stoichiometric conditions, simple allyltin or (Z) or (E)-crotyltin carbamates cleanly afford the corresponding (E9-allylic alcohols whereas less stereoselective reactions are observed with more complex substrates.

Allylic stannanes - allylic carbamates - vinylic carbamates - selenium dioxide - allylic oxidation - allylic alcohols