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.
3-Alkenyl-2-silyloxyindoles: An Enabling, Yet Understated Progeny of Vinylogous Carbon Nucleophiles / Rassu, G.; Zambrano, V.; Tanca, R.; Sartori, Andrea; Battistini, Lucia; Zanardi, Franca; Curti, Claudio; Casiraghi, Giovanni. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - (2012), pp. 466-470. [10.1002/ejoc.201101446]
3-Alkenyl-2-silyloxyindoles: An Enabling, Yet Understated Progeny of Vinylogous Carbon Nucleophiles
SARTORI, Andrea;BATTISTINI, Lucia;ZANARDI, Franca;CURTI, Claudio;CASIRAGHI, Giovanni
2012-01-01
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
