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3‐Alkenyl‐2‐silyloxyindoles: An Enabling, Yet Understated Progeny of Vinylogous Carbon Nucleophiles
Author(s) -
Rassu Gloria,
Zambrano Vincenzo,
Tanca Rossella,
Sartori Andrea,
Battistini Lucia,
Zanardi Franca,
Curti Claudio,
Casiraghi Giovanni
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101446
Subject(s) - chemistry , aldol reaction , nucleophile , selectivity , double bond , catalysis , enantioselective synthesis , organocatalysis , stereochemistry , organic chemistry , combinatorial chemistry
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.