Synthesis of Soai Aldehydes for Asymmetric Autocatalysis by Desulfurative Cross-Coupling

Palladium-catalyzed dehydrosulfurative Liebes­kind–Srogl coupling of terminal alkynes with 2-mercapto-1,3-pyrimidine-5-carbaldehyde under base-free conditions provides 2-(alkynyl)-1,3-pyrimidine-5-carbaldehydes, which are substrates for autocatalytic amplification of chirality according to Soai et a...

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Bibliographic Details
Published in:Organic letters 2014-03, Vol.16 (5), p.1282-1285
Main Authors: Maltsev, Oleg V, Pöthig, Alexander, Hintermann, Lukas
Format: Article
Language:English
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Summary:Palladium-catalyzed dehydrosulfurative Liebes­kind–Srogl coupling of terminal alkynes with 2-mercapto-1,3-pyrimidine-5-carbaldehyde under base-free conditions provides 2-(alkynyl)-1,3-pyrimidine-5-carbaldehydes, which are substrates for autocatalytic amplification of chirality according to Soai et al. The mercapto aldehyde acceptor is obtained by condensation of Arnold’s vinamidinium salt with thiourea.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500189s