Rassu, Gloria Maria Rita and Zambrano, Vincenzo and Tanca, Rossella and Sartori, Andrea and Battistini, Lucia and Zanardi, Franca and Curti, Claudio and Casiraghi, Giovanni (2012) 3-Alkenyl-2-silyloxyindoles: an enabling, yet understated progeny of vinylogous carbon nucleophiles. European Journal of Organic Chemistry, Vol. 2012 (3), p. 466-470. eISSN 1099-0690. Article.
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We introduce novel 3-alkenyl-2-silyloxyindole nucleophiles and demonstrate their utility by developing an unprecedented vinylogous Mukaiyama-type aldol reaction with aromatic aldehydes. This reaction displays excellent levels of γ- site selectivity and diastereoselectivity and delivers valuable hydroxylated oxindoles bearing a substituted exocyclic double bond at the C-3 position. A preliminary trial of an asymmetric, catalytic version was conducted, and it showed promising enantioselectivity for the desired vinylogous aldol products.
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