Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 10, Pages 1902-1907Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201636
Keywords
Alkylation; Asymmetric catalysis; C-C coupling; Hafnium; Regioselectivity
Categories
Funding
- Ministerio de Ciencia e Innovacion
- Gobierno de Espana
- FEDER
- European Union [CTQ 2009-13083]
- Generalitat Valenciana [ACOMP/2012/212, ISIC 2012/001]
- Generalitat Valenciana
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A highly enantioselective Friedel-Crafts reaction of unprotected indoles with (E)-1-aryl-4-benzyloxybut-2-en-1-ones catalyzed by a new chiral [Hf{(R)-3,3'-Br-2-BINOL}(OtBu)(2)](2) complex has been developed to functionalize the C-3 position of the indole nucleus with a side chain bearing a 1,4-difunctionalized moiety and a benzylic stereogenic center. The reaction proceeds in good to excellent yields and excellent enantioselectivities (up to 97% ee). The usefulness of this approach was illustrated with the synthesis of a tryptophol derivative.
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