Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 3, Pages 466-470Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101446
Keywords
Aldol reactions; Asymmetric catalysis; Nitrogen heterocycles; Silicon; Nucleophiles
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Funding
- Regione Autonoma della Sardegna [7]
- Universita degli Studi di Parma
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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 gamma-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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