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Rhodium-Catalyzed Enantioselective Conjugate Silyl Transfer: 1,4-Addition of Silyl Boronic Esters to Cyclic Enones and Lactones

Christian Walter, Gertrud Auer, Martin Oestreich

*Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany, Email: martin.oestreichtu-berlin.de

C. Walter, G. Auer, M. Oestreich, Angew. Chem. Int. Ed., 2006, 45, 5675-5677.

DOI: 10.1002/anie.200601747 (free Supporting Information)



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Abstract

In the presence of cationic rhodium complexes, Si-B compounds function as equivalents of nucleophilic silicon, which is efficiently transferred onto acyclic as well as cyclic α,β-unsaturated carbonyl compounds. [((S)-binap)Rh(cod)]ClO4 has effected an asymmetric 1,4-addition to cyclic acceptors in high enantiomeric excess.

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Key Words

asymmetric catalysis, boron, homogeneous catalysis, rhodium, alkylsilanes


ID: J06-Y2006-2630