Synthesis 2012; 44(23): 3590-3594
DOI: 10.1055/s-0032-1317161
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of Substituted Indoles Through Zirconium(IV)-Catalyzed Friedel–Crafts Alkylation

Gonzalo Blay
Departament de Química Orgànica, Facultat de Química, Universitat de València, C/Dr. Moliner 50, 46100 Burjassot (València), Spain , Fax: +34(963)544328   Email: [email protected]
,
Isabel Fernández
Departament de Química Orgànica, Facultat de Química, Universitat de València, C/Dr. Moliner 50, 46100 Burjassot (València), Spain , Fax: +34(963)544328   Email: [email protected]
,
José R. Pedro*
Departament de Química Orgànica, Facultat de Química, Universitat de València, C/Dr. Moliner 50, 46100 Burjassot (València), Spain , Fax: +34(963)544328   Email: [email protected]
,
Carlos Vila
Departament de Química Orgànica, Facultat de Química, Universitat de València, C/Dr. Moliner 50, 46100 Burjassot (València), Spain , Fax: +34(963)544328   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 01 June 2012

Accepted after revision: 02 August 2012

Publication Date:
23 August 2012 (online)


Abstract

The chiral complex of (R)-3,3′-Br2-BINOL and zirconium tert-butoxide catalyzes the Friedel–Crafts alkylation of indoles with enones bearing an alkyl or fluorinated group at the β-position to give indoles having a side chain at the C3 position with a tertiary stereogenic center in good yields and with excellent enantioselectivities.

 
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