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Synthesis 1995; 1995(7): 815-819
DOI: 10.1055/s-1995-4006
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A New Selective Allyl Transfer Reagent: Facile Entry to β-Hydroxy Enol Silyl Ethers Bearing Two Contiguous Stereogenic Centers

Jan Szymoniak, Hervé Lefranc, Jack Besançon, Claude Moïse*
  • *Laboratoire de Synthèse et d’Electrosynthèse Organométalliques associé au CNRS (URA 1685), Faculté des Sciences, 6 bd Gabriel, F-210000 Dijon, France, Fax +33(80)396076
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Publication Date:
31 December 2000 (online)

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η 3-Allyltitanium(III) complexes functionalized on the C-2 with a silyloxy group can be prepared by the reaction of titanocene dichloride with isopropylmagnesium chloride in the presence of the corresponding 2-silyloxybutadienes. These complexes undergo a highly regio- and diastereoselective addition with aldehydes to produce, depending on the treatment applied, anti diastereomeric β-hydroxy silyl enol ethers or β-hydroxy ketones. Two defined contiguous stereocenters make the enol silyl ethers containing them versatile synthons for further stereocontrolled transformations. The reaction constitutes a new method for directing electrophiles to the α-position of the α,β-enone system.

allylation - η 3-allyltitanium(III) complex - homoallylic alcohols - silyl enol ethers - stereocontrol