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Synthesis 2005(10): 1581-1588
DOI: 10.1055/s-2005-865294
DOI: 10.1055/s-2005-865294
PAPER
© Georg Thieme Verlag Stuttgart · New York
Palladium-Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes: A Highly Stereoselective Synthesis of 8,18-13C2-Labeled Retinal [1]
Weitere Informationen
Received
4 January 2005
Publikationsdatum:
07. April 2005 (online)
Publikationsverlauf
Publikationsdatum:
07. April 2005 (online)
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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
Labeled positions were based on the retinoid numbering system.