Download PDF
Synfacts 2011(6): 0660-0660  
DOI: 10.1055/s-0030-1259903
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

A Stereoselective Approach to Tetrasubstituted Silyl Enol Ethers

Contributor(s): Paul Knochel, Thomas Kunz
Z. Song*, L. Kui, X. Sun, L. Li
Sichuan University, Chengdu and Lanzhou University, P. R. of China
Further Information

Publication History

Publication Date:
19 May 2011 (online)

    Permissions and Reprints

Significance

This work discloses a highly ste­reoselective approach to tetrasubstituted (Z)-β-hydroxy-α-TMS silyl enol ethers. The reaction proceeds via the addition of TMS-substituted oxiranyl anions to various aliphatic, aromatic, and heterocyclic acylsilanes. A subsequent Brook rearrangement leads to an intermediary siloxy carbanion, which after an epoxide opening affords tetrasubstituted, exclusively Z-configured silyl enol ethers.