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- Title
Stereoselective Construction of 1,3-Disilylcyclopentane Derivatives by Scandium-Catalyzed [3+2] Cycloaddition of Allylsilanes to β-Silylenones.
- Authors
Okamoto, Kazuhiro; Tamura, Eisuke; Ohe, Kouichi
- Abstract
The Sc(OTf)3-catalyzed [3+2] cycloaddition of allylsilanes to β-silyl-α,β-unsaturated ketones (β-silylenones) has been developed to form five-membered syn-1,3-disilylketones diastereoselectively through the rearrangement of the silicon substituents on the allylsilane. Stabilization of the carbocation intermediates by a double silicon effect plays a key role in directing the course of the reaction to favor the [3+2] cycloaddition pathway over simple allylation.
- Subjects
STEREOSELECTIVE reactions; CYCLOPENTANE derivatives; SCANDIUM catalysts; RING formation (Chemistry); ALLYLSILANES; SILYLATION
- Publication
Angewandte Chemie, 2014, Vol 126, Issue 38, p10359
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201404218