Palladium-Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes: A Highly Stereoselective Synthesis of 8,18-13C2-Labeled Retinal

Akimori Wada; Yasuhiro Ieki; Saeko Nakamura; Masayoshi Ito

doi:10.1055/s-2005-865294

PAPER

Palladium-Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes: A Highly Stereoselective Synthesis of 8,18-¹³C₂-Labeled Retinal [1]

Akimori Wada*, Yasuhiro Ieki, Saeko Nakamura, Masayoshi Ito
Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada, Kobe 658-8558, Japan
Fax: +81(78)4417562; e-Mail: a-wada@kobepharma-u.ac.jp;

Abstract

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Abstract

Here we report that enol nonaflates exhibit higher reactivity than the corresponding enol triflates in palladium-catalyzed cross-coupling reactions with various (vinyl)tributylstannanes and acetylenes. We also highlight the reaction of a vinyl nonaflate, containing two ¹³C-labeled carbon atoms with an alkenyl stannane, which afforded the trisubstituted E-olefin stereoselectively in high yield. The E-olefin was then transformed into the corresponding all-E-retinal.

Key words

alkenyl stannane - coupling reaction - labeled retinal - solid-state NMR - vinyl nonaflate

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References

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Labeled positions were based on the retinoid numbering system.

Palladium-Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes: A Highly Stereoselective Synthesis of 8,18-13C2-Labeled Retinal [1]

Palladium-Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes: A Highly Stereoselective Synthesis of 8,18-¹³C₂-Labeled Retinal [1]