Curti, Claudio and Battistini, Lucia and Sartori, Andrea and Lodola, Alessio and Mor, Marco and Rassu, Gloria Maria Rita and Pelosi, Giorgio and Zanardi, Franca and Casiraghi, Giovanni (2011) Catalytic, asymmetric hypervinylogous Mukaiyama aldol reactions of extended furan-based silyl enolates. Organic Letters, Vol. 13 (17), p. 4738-4741. ISSN 1523-7060. eISSN 1523-7052. Article.
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Virtually perfect transmittal of the enolate reactivity up to five conjugated double bonds from the origin allows a series of furan-based silyloxypolyenes to add to aldehyde carbonyls at the most distant point of the molecule. Denmark’s axially chiral bisphosphoramide/SiCl4 combination catalyzes these scantly precedented, long-range Mukaiyama-type vinylogous aldol reactions efficiently, providing a palette of extended γ-alkylidene butenolide carbinols with complete ω-site selectivity and good to excellent levels of enantioselectivity.
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