A New Selective Allyl Transfer Reagent: Facile Entry to β-Hydroxy Enol Silyl Ethers Bearing Two Contiguous Stereogenic Centers
- 1 July 1995
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1995 (07) , 815-819
- https://doi.org/10.1055/s-1995-4006
Abstract
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.Keywords
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