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

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

References

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19

Labeled positions were based on the retinoid numbering system.