Publication: A novel stereoselective reaction cascade leading from $\alpha$-silylated allylic alcohols to aldol-type products
A novel stereoselective reaction cascade leading from $\alpha$-silylated allylic alcohols to aldol-type products
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Fässler, J., Enev, V., & Bienz, S. (1999). A novel stereoselective reaction cascade leading from $\alpha$-silylated allylic alcohols to aldol-type products. Helvetica Chimica Acta, 82(4), 561–587. https://doi.org/10.1002/(SICI)1522-2675(19990407)82:4<561::AID-HLCA561>3.0.CO;2-U
Abstract
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Abstract
The treatment of a-silylated allylic alcohols with epoxidizing reagents afforded in a highly stereocontrolled fashion a-silylated aldols. The transformation is proposed to proceed either by a reaction cascade involving stereospecific epoxidation of the allylic-alcohol moiety followed by an acid-supported pinacol-type rearrangement, or by a sequence consisting of a p-face-selective electrophilic attack at the allylic silane moiety with hyperconjugative stabilization of the evolving carbocation, followed by rearrangement of the thus obt
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- Fässler, Jürg
- Enev, Valentin
- Bienz, Stefan
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Fässler, J., Enev, V., & Bienz, S. (1999). A novel stereoselective reaction cascade leading from $\alpha$-silylated allylic alcohols to aldol-type products. Helvetica Chimica Acta, 82(4), 561–587. https://doi.org/10.1002/(SICI)1522-2675(19990407)82:4<561::AID-HLCA561>3.0.CO;2-U
