Synthesis of Functionalized Allylsilicone Compounds via Rhodium-Catalyzed Conjugate Addition of (E)- or (Z)-[3-Trimethylsilyl-1-propenyl]boronic Acids to Enones

Yasunori Yamamoto; Masayoshi Fujita; Norio Miyaura

doi:10.1055/s-2002-25371

LETTER

Synthesis of Functionalized Allylsilicone Compounds via Rhodium-Catalyzed Conjugate Addition of (E)- or (Z)-[3-Trimethylsilyl-1-propenyl]boronic Acids to Enones

Yasunori Yamamoto, Masayoshi Fujita, Norio Miyaura*
Division of Molecular Chemistry; Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
Fax: +81(11)7066561; e-Mail: miyaura@org-mc.eng.hokudai.ac.jp;

Abstract

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Abstract

The rhodium-catalyzed conjugate addition of (E)-Me₃SiCH₂CH=CHB(iPrO)₂ or (Z)-Me₃SiCH₂(C₄H₉)C=CHB(iPrO)₂ to enones provided a novel method for the synthesis of allylsilicone compounds possessing a carbonyl group in the same molecule, which are versatile intermediates for intramolecular allylsilylation, giving cyclobutanols on treatment with Bu₄NF.

Key words

allylsilicone - alkenylboronic acid - rhodium catalyst - conjugate addition - cyclobutanol

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Referenzen

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