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Triphenylphosphine Oxide-Catalyzed Selective α,β-Reduction of Conjugated Polyunsaturated Ketones

Xuanshu Xia, Zhiqi Lao, Patrick H. Toy*

*Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China, Email: phtoyhku.hk

X. Xia, Z. Lao, P. H. Toy, Synlett, 2019, 30, 1100-1104.

DOI: 10.1055/s-0037-1611537 (free Supporting Information)


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Abstract

In a triphenylphosphine oxide-catalyzed reduction of conjugated polyunsaturated ketones using trichlorosilane as reducing reagent, the α,β-C=C double bond was selectively reduced while all other reducible functional groups remained unchanged. Additionally, a tandem one-pot Wittig/conjugate-reduction reaction sequence provides γ,δ-unsaturated ketones from simple building blocks.

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Key Words

triphenylphosphine oxide, trichlorosilane, 1,4-reduction, Lewis base, organocatalysis, pheromones


ID: J72-Y2019